Hydrochloric Acid → 12-Cyclohexyl-6H-indolo[1,2-c][1,3]benzoxazine-9-carboxylic acid

HRID 1012255Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[C:13]([N:14]4[C:19]=2[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]4)=[CH:12][C:11]([C:24]([O:26]C)=[O:25])=[CH:10][CH:9]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1.CO>[CH:1]1([C:7]2[C:8]3[C:13]([N:14]4[C:19]=2[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]4)=[CH:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][CH:9]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 11-cyclohexyl-5-oxa-6a-azabenzo[a]fluorene-8-carboxylate (40 mg, 0.11 mmol) in tetrahydrofuran (1 ml) and methanol (1 ml) was added 4N aqueous sodium hydroxide solution (1 ml), and the mixture was stirred at 60° C. for 3 hr. 1N Hydrochloric acid was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with hexane and dried in vacuo to give 11-cyclohexyl-5-oxa-6a-azabenzo[a]fluorene-8-carboxylic acid (26 mg, yield 68.4%).

Workup

filtrationthe precipitated solid was collected by filtration
washwashed with hexane
customdried in vacuo

Sources & evidence

ORD record: ord-8c721547a6ac47cfb7ab077183e50b65
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977331B1

Reaction notes

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