Acetic Anhydride → HCID 14529092, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[CH:2]1.[C:11](OC(=O)C)(=[O:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:10][C:11](=[O:13])[CH3:12])[CH:8]=2)[CH:3]=[CH:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1H-indol-6-ol (1.5 g, 11.4 mmol) and acetic anhydride (1.2 mL, 12.6 mmol) in DCM (114 mL) was added Et3N (3.18 mL, 22.8 mmol) and the reaction mixture was stirred (rt, 64 h). The reaction mixture was washed with H2O (4×25 mL) and brine (50 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound (2.0 g, 100%). MS (ESI): mass calculated for C10H9NO2, 175.1; m/z found, 176.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.23 (s, 1H), 7.62 (d, J=8.5, 1H), 7.21 (dd, J=3.2, 2.4, 1H), 7.18-7.15 (m, 1H), 6.87 (dd, J=8.5, 2.1, 1H), 6.55 (ddd, J=3.1, 2.0, 0.9, 1H), 2.35 (s, 3H).