Acetic Anhydride → HCID 14529092, compound

HRID 1947448Notes

Reaction equation

HRID 1947448 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]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5245086-Hydroxyindole

Product 1

HCID 14529092HCID 14529092, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. washThe reaction mixture was washed with H2O (4×25 mL) and brine (50 mL)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1311066c875745b783b51173eaa630ae
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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