Potassium Carbonate → HCID 18439654, compound

HRID 457476Notes

Reaction equation

[C:1]([N:4]1[CH:10]([CH3:11])[CH2:9][C:8]2[CH:12]=[C:13](Br)[C:14]([O:16][CH3:17])=[CH:15][C:7]=2[C:6]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[C:21]([CH3:28])[CH:20]=2)=[N:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O.NN>COCCO.[Pd]>[C:1]([N:4]1[CH:10]([CH3:11])[CH2:9][C:8]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:7]=2[C:6]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH3:28])[CH:20]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

4.46 g (10 mmoles) of (±)-3-acetyl-7-bromo4,5-dihydro-1-(3-methyl-4-nitrophenyl)-4-methyl-8-methoxy-3H-2,3-benzo-diazepine are dissolved in 190 cm3 of methyl cellosolve, then 2.1 g (15 mmoles) of potassium carbonate and 1.8 g of 10% palladium/charcoal catalyst and, under vigorous stirring, 1.95 cm3 (40 mmoles) of 98% hydrazine hydrate are added. The reaction mixture is stirred at 100° C. for 1 hour, the catalyst is filtered, the filtrate is evaporated, and the residue is rubbed with 50 cm3 of water to obtain solid matter. The crude product is purified by chromatography over a column containing silica gel and using a mixture of ethyl acetate and hexane, then the product is recrystallized from acetonitrile. Thus, 1.6 g (47%) of the title compound are obtained in the form of cream coloured solids melting at 169–171° C.

Workup

filtrationthe catalyst is filtered
customthe filtrate is evaporated
customto obtain solid matter
customThe crude product is purified by chromatography over a column
additioncontaining silica gel
additiona mixture of ethyl acetate and hexane
customthe product is recrystallized from acetonitrile

Sources & evidence

ORD record: ord-073794813ba24374bfc5bbb528b0df5d
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189711B2

Reaction notes

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