Benzoylacetone → (4-amino-2-methyl-5-phenyl-1H-pyrrol-3-yl)-phenylmethanone

HRID 2049733Notes

Reaction equation

HRID 2049733 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[N:4].[C:11]([CH2:19][C:20](=O)[CH3:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)C.CCCCCC>[NH2:4][C:3]1[C:19]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:20]([CH3:21])[NH:1][C:2]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 408382-Amino-2-phenylacetonitrile

Product 1

HCID 3042143(4-amino-2-methyl-5-phenyl-1H-pyrrol-3-yl)-phenylmethanone

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

Starting from 2-amino-2-phenylacetonitrile and benzoylacetone, the open-chain intermediate compound is obtained, melting at 134°-135° C. (from diethyl ether/hexane). The title compound is obtained in a 60% overall yield. M.P. 285°-290° C. (from methanol/diethyl ether). The free base melts at 203°-5° C. (from methanol).

Workup

  1. customthe open-chain intermediate compound is obtained

Sources & evidence

ORD record
ord-37de0f06b8684a3297449ac6f88d4493
Source dataset
uspto-grants-1980_04
Patent number
US04198502

Reaction notes

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