Ammonium Hydroxide → 4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline

HRID 369383Notes

Reaction equation

[C:1]([C:9]1[N:13]([CH3:14])[C:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+]>CO.Cl.B#[Ni]>[C:1]([C:9]1[N:13]([CH3:14])[C:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)=[CH:11][C:10]=1[CH3:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a slurry of 4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]nitrobenzene (3.55 g, 10.6 mmol) [prepared as in Example 2, Step (a)] in methanol (170 ml) and hydrochloric acid (50 ml, 1M) was added nickel boride (3.41 g, 26.6 mmol), and the mixture was stirred at 75° C. for 15 h. The reaction mixture was cooled, basified with ammonium hydroxide and the product was extracted into ethyl acetate. The organic phase was washed with water and dried over sodium sulfate. Evaporation of the solvent gave 4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (3.11 g, 96%) as a pale yellow solid.

Workup

temperatureThe reaction mixture was cooled
extractionthe product was extracted into ethyl acetate
washThe organic phase was washed with water
dry with materialdried over sodium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-1bef74759a994ed8b85dfc7f695aff63
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136844

Reaction notes

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