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CAS No. : | 659737-57-2 | MDL No. : | MFCD08276013 |
Formula : | C8H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YGEDYDDFFVHFEA-UHFFFAOYSA-N |
M.W : | 149.15 | Pubchem ID : | 11528364 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | A mixture [OF 6-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE] (167 mg, 1.0 mmol) and boron tri- bromide (1 M in [CH2C12,] 3.6 mL, 3.6 mmol) in [CH2CI2] (8 mL) [AT-78C] was stirred for 18 h at RT. The mixture was then cooled to-78C and [MEOH] (20 mL) was added. After 2 h at-78C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2CL2] : 2N NH3-MeOH 9: 1) to afford the title product (147 mg, 100%) as a white solid. MS m/e = 148.0 (M-H+). | |
95% | 6-Hydroxy-2,3-dihydro-isoindol-1-one<strong>[22246-66-8]6-Methoxy-2,3-dihydro-isoindol-1-one</strong> (90 g, 0.55 moles, 1 equiv) was suspended in 2.52 L of DCM and 661 mL of BBr3 ( 0.66 moles, 1.2 equiv, 1.0 M solution in DCM) was added over 2 h at 0 0C. After the addition was complete, the reaction mixture was allowed to warm to room temperature over 3 h then stirred overnight. The reaction mixture was quenched by the addition of 1 L of MeOH at 0 0C and then stirred at room temperature for 3 h.Solvent was evaporated under vacuum, and the crude material was triturated with minimum amount of MeOH (-400 mL). The solid was filtered and dried under vacuum at 50 0C for 24 h to give 46.3 g of 6-Hydroxy-2,3-dihydro-isoindol-1-one with >98 % purity (56%). The mother liquor was concentrated and triturated with minimum amount of MeOH to afford 32 g of additional 6-Hydroxy-2,3-dihydro-isoindol-1-one with >90 % purity (39%). | |
79% | With methanesulfonic acid; DL-methionine; at 85℃; for 24h;Product distribution / selectivity; | Alternatively, to a flask containing <strong>[22246-66-8]6-Methoxy-2,3-dihydro-isoindol-1-one</strong> (435 mmol, 71.0 g) and methionine (771 mmol, 115 g) was added methanesulfonic acid (9.15 mol, 600 mL, 880 g). The reaction was stirred at 85 0C for 24 h and then was cooled and 1 L of water was slowly added to the mixture which caused an exotherm. The mixture was cooled to 5 0C. A tan solid was recovered via filtration, washed with water containing 1% HCI, water, and then dried- in vacuum oven at 45 0C overnight to afford 6-Hydroxy-2,3-dihydro-isoindol-1-one (51.4 g, 79%). MS: ES: M+1: 164.0 (163.1 ) 1H NMR (400 MHz, DMSO-d6) delta ppm 3.76 (s, 3 H) 4.23 (S, 2 H) 7.07-7.12 (m, 2H) 7.41 (d, J=8.97 Hz, 1 H) 8.47 (s, 1 H) |
78% | To a suspension of (74) (7.07 g, 43.4 mmol) in CH2Cl2 (600 ml) was added BBr3(IM in CH2Cl2, 86.7 ml). The reaction mixture was stirred at room temperature for 4 hr. The solvent and boron residue was removed in vacuo and the remaining solid was dissolved in CH2Cl2, the solution was neutralized with 1 N NaOH (PH = 6.5). Desired compound was precipitated out and filtered. The organic solution was separated and washed with sat. NaCl, dried over Na2SO4 to give the title compound (combined weight 5.1 g, 78 %). MS (ES) m/z 150.1. | |
With boron tribromide; In dichloromethane; at -78 - 20℃;Heating / reflux; | Scheme 9Intermediate 23:Example Compound 13 (150 mg, 0.92 mmol) was dissolved in DCM (20 mL) and cooled to -78 C. To this mixture, BBr3 (1 M, 1.2 mL) was added dropwise. <n="76"/>After 1 hour, the mixture was warmed to room temperature and stirred for another 2 hours. Then, another portion of BBr3 (1 M, 1.2 ml_) was added and the resulting mixture was heated to reflux and stirred overnight. After cooling to room temperature, EtOAc (100 ml_) was added and the organics washed with water, brine and dried over Na2SO4. After concentration, the residue was used in the next step without further purification. HPLC-MS tR = 0.58 min (UV254 nm); mass calculated for formula C8H7NO2 149.0, observed LCMS m/z 150.1 (M+H). |
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