Hydrochloric Acid → 3-{5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-yl-methyl}aniline

HRID 369396Notes

Reaction equation

[CH3:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:16]=[C:17]([N+:21]([O-])=O)[CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl.[OH-].[NH4+]>B#[Ni].CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[NH2:21])=[CH:10][CH:9]=2)=[O:7])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 3-{5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}-nitrobenzene (0.86 g, 2.6 mmol) [prepared as in Example 8, Step (c)], nickel boride (1.0 g), 10% HCl (13 ml), and methanol (35 ml) was heated at 65° C. for 40 min. The reaction mixture was cooled to room temperature, made basic with concentrated ammonium hydroxide, and filtered through Celite®. The product was extracted into ethyl acetate, and the organic extracts were washed with water and brine, and dried over sodium sulfate. Evaporation of the organics gave 3-{5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-yl-methyl}aniline (0.73 g, 99%) as a solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through Celite®
extractionThe product was extracted into ethyl acetate
washthe organic extracts were washed with water and brine
dry with materialdried over sodium sulfate
customEvaporation of the

Sources & evidence

ORD record: ord-05cb480112d84d6bad91a91f945848c0
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136844

Reaction notes

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