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

HRID 365602Notes

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-da0823ad8a5e4926a2a292473b8e7144
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127402

Reaction notes

Loading…