Methanol → HCID 59478087, compound

HRID 1516599Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]([C:22]#[N:23])=[CH:12]2)=[CH:7][C:6]=1[N+:24]([O-])=O)[CH3:2].CO>[C].[Pd].C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]([C:22]#[N:23])=[CH:12]2)=[CH:7][C:6]=1[NH2:24])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(3-cyano-4-phenylpyrrole-1-yl)-2-nitro-benzoic acid ethyl ester (0.090 g) in a mixed solvent of methanol (2.5 mL) and ethyl acetate (2.5 mL) was added 10% palladium-carbon powder (0.016 g) under an argon atmosphere, and this mixture was stirred at 40° C. under a hydrogen atmosphere for 3 hours. After this reaction mixture was replaced under an argon atmosphere, the insoluble material was removed by suction through a Celite pad. This filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane=50/50) to give the title compound (0.070 g).

Workup

customthe insoluble material was removed by suction through a Celite pad
concentrationThis filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane=50/50)

Sources & evidence

ORD record: ord-5c9c91f8c1e5416f89596021d0dedc44
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227500B2

Reaction notes

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