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

HRID 1748266Notes

Reaction equation

[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([O:18]CC)=[O:17])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.[OH-].[Na+].Cl>C1COCC1.CO.O>[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of ethyl 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate (900 mg, 3.3 mmol) in THF:methanol (1:1, 20 mL) is added 1N NaOH (9.0 mL, 9.0 mmol). The reaction mixture is heated at 70° C. for 2 h. The reaction mixture is cooled to room temperature, diluted with water (80 mL) and is acidified with 3N HCl to pH 2-3. The resulting yellow precipitate is filtered, washed with water and dried in vacuo oven at 60° C. to afford the title compound (540 mg, 67%).

Workup

temperatureThe reaction mixture is cooled to room temperature
filtrationThe resulting yellow precipitate is filtered
washwashed with water
customdried in vacuo oven at 60° C.

Sources & evidence

ORD record: ord-e79230f1d0ed45c5a4ce4cd858210cd3
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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