2-Chloro-6-methylaniline → HCID 20484357, compound

HRID 437977Notes

Reaction equation

HRID 437977 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)([O-])O.[Na+].[CH3:15][O:16][C:17](=[O:21])[CH:18](Br)[CH3:19]>>[CH3:15][O:16][C:17](=[O:21])[CH:18]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[Cl:1])[CH3:19]

Participants

4

Reactant 3

HCID 68972-Chloro-6-methylanilineHCID 95576Methyl 2-bromopropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 20484357HCID 20484357, compound

Procedure

35.4 g of 2-chloro-6-methylaniline, 21.3 g of sodium hydrogen carbonate and 84 ml of DL-α-bromopropionic acid methyl ester are stirred for 17 hours at 140° bath temperature. After cooling, the darkly coloured reaction mixture is filtered, and the excess α-bromopropionic acid methyl ester is distilled off in a water-jet vacuum. The residue remaining is fractionally distilled in high vacuum. There is obtained 25.9 g of α-(2-chloro-6-methylanilino)-propionic acid methyl ester, b.p. 72°-75°/0.001 Torr.

Workup

  1. temperatureAfter cooling
  2. filtrationthe darkly coloured reaction mixture is filtered
  3. distillationthe excess α-bromopropionic acid methyl ester is distilled off in a water-jet vacuum
  4. distillationThe residue remaining is fractionally distilled in high vacuum

Sources & evidence

ORD record
ord-d18a7845efde4d9b9113c9f5cac4513c
Source dataset
uspto-grants-1977_06
Patent number
US04032657

Reaction notes

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