Benzoyl chloride → 5-Benzamidoindan-1-one

HRID 991005Notes

Reaction equation

HRID 991005 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C(N(CC)CC)C>[C:12]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 3128905-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 184158665-Benzamidoindan-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

5-Aminoindan-1-one (2.5 g) was reacted with benzoyl chloride (2.63 g) in dichloromethane and triethylamine to give 5-benzamidoindan-1-one which was reacted with benzaldehyde in a similar manner to Example 7a) to give N-(2-benzylidene-1-oxoindan-5-yl)benzamide which was reacted with hydrogen peroxide in a similar manner to Example 7b) to give an intermediate which was reacted with hydrazine hydrate in a similar manner to Example 7c) to give -(3N-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)benzamide, m.p. 271° C., after chromatography of the reaction mixture.

Sources & evidence

ORD record
ord-c6c0c82326a44680a31902feb567a932
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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