2,6-Dimethylaniline → Methyl N-(2,6-dimethylphenyl)-DL-alaninate

HRID 443600

Reaction equation

HRID 443600 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)(O)[O-].[Na+].Br[CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18]>>[CH3:20][O:19][C:17]([CH:16]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])[CH3:21])=[O:18]

Participants

4

Reactant 3

HCID 68962,6-DimethylanilineHCID 95576Methyl 2-bromopropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 94555Methyl N-(2,6-dimethylphenyl)-DL-alaninateYield 79.6%

Procedure

Furthermore, the reaction of 2,6-dimethylaniline at 120°-125° C., in the presence of sodium bicarbonate as an acid-binding agent, with a three-fold molar excess of methyl 2-bromopropionate has been disclosed in U.S. Pat. No. 4,008,066. With this process, N-(1'-methoxycarbonylethyl)-2,6-dimethylaniline is obtained in a yield of 79.6% of theory.

Sources & evidence

ORD record
ord-6f962d8509e74197826dff60cf811abf
Source dataset
uspto-grants-1981_04
Patent number
US04260782

Linked notes

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