Acetic Acid → 4-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid

HRID 1748284Notes

Reaction equation

[CH3:1][CH:2]1[CH2:20][N:7]2[C:8]3[CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:21])[NH:4][CH2:3]1.[OH-].[Na+].C(O)(=O)C.O>C(O)C>[CH3:1][CH:2]1[CH2:20][N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:21])[NH:4][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution ethyl 4-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate (1.4 g, 4.9 mmol) in ethanol (50 mL) is added 1M NaOH (12.5 mL, 12.5 mmol) and the mixture is heated at 80° C. for 2 h. Acetic acid (10 mL) and water (650 mL) are added and the resulting solid is filtered and rinsed with water to afford the title compound (751 mg, 58%) as a white solid.

Workup

filtrationthe resulting solid is filtered
washrinsed with water

Sources & evidence

ORD record: ord-38e78e5115b148a892bc3c66056a2b18
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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