4-Chloroaniline → N-(4-chlorophenyl)isoleucine

HRID 1389357Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Na].Br[CH:11]([CH:15]([CH3:18])[CH2:16][CH3:17])[C:12]([OH:14])=[O:13]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C@H:11]([C:12]([OH:14])=[O:13])[C@H:15]([CH2:16][CH3:17])[CH3:18])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 78124-Chloroaniline

HCID 2604812-Bromo-3-methylpentanoic acid

HCID 5360545Sodium

Product 1

HCID 54011701N-(4-chlorophenyl)isoleucine

Procedure

N-(4-chlorophenyl)isoleucine is prepared by the reaction of 4-chloroaniline with the sodium salt of α-bromo-3-methylpentanoic acid neat at 100°.

Sources & evidence

ORD record: ord-a81646a5d97748778422040a5719638b
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243819

Reaction notes

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