Potassium Carbonate → HCID 18439651, compound

HRID 457477Notes

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]([Cl: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]([Cl:28])[CH:20]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

4.66 g (10 mmoles) of (±)-3-acetyl-7-bromo-4,5-dihydro-1-(3-chloro-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 90° C. for 0.5 hours, 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 ethanol. Thus, 1.1 g (30%) of the title compound are obtained in the form of white solids melting at 152–155° 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 ethanol

Sources & evidence

ORD record: ord-873e0e9a76834f90a400fa60d2f56e50
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189711B2

Reaction notes

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