Sodium Carbonate Decahydrate → 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde-3-oxime

HRID 67296

Reaction equation

[OH2:1].O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+].[F:17][C:18]1[CH:19]=[CH:20][C:21]2[N:27]3[CH:28]=[N:29][C:30]([CH:31]=O)=[C:26]3[CH2:25][N:24]([CH3:33])[C:23](=[O:34])[C:22]=2[CH:35]=1.Cl.[NH2:37]O>O>[F:17][C:18]1[CH:19]=[CH:20][C:21]2[N:27]3[CH:28]=[N:29][C:30]([CH:31]=[N:37][OH:1])=[C:26]3[CH2:25][N:24]([CH3:33])[C:23](=[O:34])[C:22]=2[CH:35]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4.14 g (14.5 mmol) of sodium carbonate decahydrate in 20 ml of water is added dropwise to a mixture of 3.0 g (11.6 mmol) of 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde, 0.99 g (14.5 mmol) of hydroxylamine hydrochloride and 60 ml of water, the mixture is stirred at 70° C. for 1 hour, cooled in an ice-bath and the separated material is filtered off under suction and washed with water. The still moist substance is recrystallised from ethanol and yields 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde-3-oxime of melting point 247°-250° C.

Workup

temperaturecooled in an ice-bath
filtrationthe separated material is filtered off under suction
washwashed with water
customThe still moist substance is recrystallised from ethanol

Sources & evidence

ORD record: ord-b766bb24bbaa4517a10f7e16d310989a
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04346030

Linked notes

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