Methyl 2-hydroxy-2-(4-methoxyphenyl)acetate → N-(2-chloro-3,4-dimethoxyphenylethyl)-4-methoxymandelamide

HRID 486375Notes

Reaction equation

HRID 486375 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH2:14].[CH3:15][O:16][C:17]1[CH:28]=[CH:27][C:20]([CH:21]([OH:26])[C:22](OC)=[O:23])=[CH:19][CH:18]=1>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][C:22](=[O:23])[CH:21]([C:20]1[CH:27]=[CH:28][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[OH:26]

Participants

4

Reactant 2

HCID 523496Methyl 2-hydroxy-2-(4-methoxyphenyl)acetateHCID 30177522-Chloro-3,4-dimethoxyphenethylamine

Product 1

HCID 13697589N-(2-chloro-3,4-dimethoxyphenylethyl)-4-methoxymandelamideYield 69.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

16.86 g of (2-chloro-3,4-dimethoxyphenyl)ethylamine obtained in step 4 was reacted with 15.33 g of methyl 4-methoxymandelate obtained in step 5 at 130° to 140° C. in a nitrogen gas atmosphere for 1.5 hour. After cooling, the reaction mixture was dissolved in 30 ml of ethyl acetate and purified by silica gel chromatography. After development with ethyl acetate/n-hexane (1/1) and then with ethyl acetate, 20.6 g (69%) of N-(2-chloro-3,4-dimethoxyphenylethyl)-4-methoxymandelamide was obtained.

Workup

  1. temperatureAfter cooling
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-827adb5039cf44319fd43a564404c0cf
Source dataset
uspto-grants-1994_03
Patent number
US05292521

Reaction notes

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