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CAS No. : | 3373-00-0 | MDL No. : | MFCD00800243 |
Formula : | C9H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CTJSPUFGQNVJJP-UHFFFAOYSA-N |
M.W : | 149.19 | Pubchem ID : | 76897 |
Synonyms : |
|
Chemical Name : | 6-Hydroxy-1,2,3,4-tetrahydroquinoline |
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 |
---|---|---|
With hydrogen;palladium(IV) oxide; In methanol; | The starting material was prepared as follows: 6-Hydroxyquinoline (1 g, 6.9 mmol) was dissolved in methanol and hydrogenated at 3 atmospheres pressure with platinum(IV) oxide (276 mg) over 24 hours. The catalyst was removed by filtration over a pad of celite and the solvent was evaporated. The solid was washed with ether to give 6-hydroxy-(1,2,3,4)-tetrahydroquinoline (698 mg, 68 %). 1H NMR Spectrum (DMSOd6) 1.75 (m, 2H); 2.60 (m, 2H); 3.05 (m, 2H); 4.90 (br s, 1H); 6.30 (m, 3H); 8.25 (br s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.9 In analogy to example 1.8, 6-(5-Bromo-pentyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester and N-allylmethylamine were converted to yield 6-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester as colorless oil, MS: 443 (MH+, 1Cl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.7% | With sodium hydroxide; In 1,4-dioxane; water; at 20℃; | Procedure E: 1, 2,3, 4-tetrahydro-quinolin-6-ol (CAS Registry Number 3373-00-0) (25 g, 172.9 mmol) is treated with di-tert-butyl dicarbonate (56.6 g, 259.4 mmol) in a solvent mixture of dioxane (200 mL) and 1N [NAOH] (200 [ML),] and reaction mixture allowed to stir at room temperature overnight. The layers are separated, and the aqueous layer is washed with ethyl acetate (2X). The organic layers are combined and washed with brine [(1X),] dried over [NA2S04] and the organic layer evaporated to give a crude oil. Flash chromatography (Biotage, 10% EtOAc/hexanes) gives the desired material (33.0 g, 76.7% yld). |
With triethylamine; for 2.0h;Heating / reflux;Product distribution / selectivity; | 6-Hydroxy-l,2,3,4-tetrahydro quinoline (1 eq), Boc anhydride (1.2 eq) and triethyl amine (1.2 eq) were mixed and heated to refluxed for 2hr. Mixture was quenched in water and product was extracted with EtOAc to afford title compound as oil.Compound was used directly for the next reaction without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.11% | With boron tribromide; In dichloromethane; at 0 - 15℃; for 2.0h; | Compound 26A (3.00 g, 18.38 mmol) was dissolved in 50 ml of dichloromethane, BBr3 (13.81 g, 55.14 mmol)was added at 0 C, and then stirred at 15 C for 2 hours. The reaction solution was concentrated and the reaction wasquenched by 5 ml of methanol. Saturated sodium bicarbonate solution (20 ml) was added and stirred for 30 min, thenextracted with 20 ml of ethyl acetate three times. The organic phases were combined and dried over anhydrous sodiumsulfate and concentrated to give a crude product. The crude product was purified by silica gel column chromatography(petroleum ether/ethyl acetate was from 3:1 to 1:1) to give compound 26B (1.95 g, the yield was 71.11%).1H NMR (400 MHz, DMSO-d6) 8.24 (s, 1H), 6.22-6.35 (m, 3H), 4.93 (br. s., 1H), 3.02-3.10 (m, 2H), 2.57 (t, J = 6.4 Hz,2H), 1.67-1.80 (m, 2H). |
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