4-(4-Bromophenyl)butanoyl chloride → 4-{4-[4-(4-Bromo-phenyl)-butyrylamino]-phenyl}-4-oxo-butyric acid

HRID 1264103Notes

Reaction equation

HRID 1264103 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:28])[CH2:22][CH2:23][C:24]([O:26]C)=[O:25])=[CH:17][CH:16]=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:28])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:20]=2)=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2467764-(4-Bromophenyl)butanoyl chlorideHCID 12016833Methyl 4-(4-aminophenyl)-4-oxobutanoate

Product 1

HCID 102021324-{4-[4-(4-Bromo-phenyl)-butyrylamino]-phenyl}-4-oxo-butyric acidYield 85.1%

Procedure

In a manner similar to that described in Example 3, 4-(4-bromo-phenyl)-butyryl chloride (0.086 g, 0.00033 mol) was allowed to react with 4-(4-amino-phenyl)-4-oxo-butyric acid, methyl ester (0.052 g, 0.00025 mol), and the resulting intermediate was hydrolyzed to give 0.089 g of 4-{4-[4-(4-bromo-phenyl)-butyrylamino]-phenyl}-4-oxo-butyric acid as a yellow solid; MS-(AP+) MH+419.

Sources & evidence

ORD record
ord-5c1f2327029b48e0a070d1897e81cdf1
Source dataset
uspto-grants-2003_04
Patent number
US06541521B1

Reaction notes

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