2-Acetoxybenzoyl chloride → HCID 20298463, compound

HRID 1389220Notes

Reaction equation

HRID 1389220 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(C(C)C)C(C)C)C.[C:32]([O:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](Cl)=[O:39])(=[O:34])[CH3:33]>C1C=CC=CC=1>[C:32]([O:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([N:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:39])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 796682-Acetoxybenzoyl chlorideHCID 81531DiisopropylethylamineHCID 20298423HCID 20298423, compound

Product 1

HCID 20298463HCID 20298463, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

15.0 g of ethyl 5-(biphenyl-2-yl)aminovalerate is reacted, analogously to Example 47b), with 6.6 g of ethyldiisopropylamine and 10.0 g of o-acetoxybenzoylchloride in 70 ml of benzene to obtain, as reaction product, 17.0 g (73.4% of theory) of ethyl 5-[o-acetoxy-N-(biphenyl-2-yl)-benzamido]valerate as a viscous non-distillable oil. The saponification of this ester yields 9.1 g (63.2% of theory) of 5-[o-hydroxy-N-(biphenyl-2-yl)benzamido]valeric acid, MP 138° to 139°.

Sources & evidence

ORD record
ord-b450b5fd7df44297890e7212de7103f5
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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