ChemicalBook CAS DataBase List 1,3,3-TRIMETHYLINDOLINOBENZOPYRYLOSPIRAN

1,3,3-TRIMETHYLINDOLINOBENZOPYRYLOSPIRAN synthesis

7synthesis methods

Product Name:1,3,3-TRIMETHYLINDOLINOBENZOPYRYLOSPIRAN
CAS Number:1485-92-3
Molecular formula:C19H19NO
Molecular Weight:277.36

5418-63-3
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90-02-8 Synthesis

90-02-8
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1,3,3-TRIMETHYLINDOLINOBENZOPYRYLOSPIRAN

1485-92-3
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$31.00/1g

Yield: 81%

Reaction Conditions:

with cholin hydroxide in water at 80; for 1 h;Reagent/catalyst;Solvent;Time;Temperature;

Steps:

General experimental procedure for the synthesis of spiropyrans
General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).Characterization data for selected spiropyran(SP-1): 10,30,30-trimethylspiro[chromene-2,20-indoline]81%; Colorless solid; M.P. 91-92 °C. Reported M.P. 92-94 °C.[25]1H NMR (200 MHz) δ 7.23 (1H, d, J 8.0 Hz, C5-H), 7.06-6.96 (5H, m, C4-H, C8-H,C60-H, C40-H & C7-H), 6.83-6.70 (2H, m, C50-H & C6-H), 6.61 (1H, d, J 8.0 Hz,C70-H), 5.69 (1H, d, J 10.0 Hz, C3-H), 2.57 (3H, s, N-CH3), 1.32 (3H, s, C30-CH3),1.10 (3H, s, C30-CH3). 13C NMR: δ 154.64 (C8-C-O), 148.43 (C70-C-N), 136.28 (C30-CC40),129.57 (C5), 129.40 (C7), 127.37 (C3 & C40), 126.65 (C60), 120.55 (C4-C-C5),119.88 (C4), 119.55 (C6), 118.22 (C50), 114.79 (C8), 106.85 (C70), 105.18 (C2), 51.61(C30), 29.66 (N-CH3), 25.69 (C30-CH3), 20.17 (C30-CH3).LC-MS (m/z): Calculated for C19H20NO (MH) 278.2, Observed 278.2

References:

Pargaonkar, Jyotsna G.;Patil, Sanjay K.;Vajekar, Shailesh N. [Synthetic Communications,2018,vol. 48,# 2,p. 208 - 215] Location in patent:supporting information

118-12-7 Synthesis