P-Anisidine → 3-Chloro-n-(4-methoxyphenyl)propanamide

HRID 431809Notes

Reaction equation

HRID 431809 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CCN(CC)CC.[Cl:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>C(C(C)=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:20](=[O:21])[CH2:19][CH2:18][Cl:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 693643-Chloropropionyl chloride

Product 1

HCID 5320593-Chloro-n-(4-methoxyphenyl)propanamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
10 °C

Procedure

A three-necked flask-was charged with p-Anisidine (50 g), Et3N (40.43 g) and methyl ethyl ketone (100 ml). The resulting slurry was cooled to 10° C. and 3-chloropropionyl chloride (50.74 g) was slowly added. The temperature was allowed to rise to 60° C. during the addition. The mixture was then refluxed for 1 hour and cooled to 50° C. The solids were collected by filtration, washed with water, and dried at 50° C. to constant weight to give N-(4-methoxyphenyl)-3-chloropropionamide (56.42 g, 86.8%).

Workup

  1. additionto rise to 60° C. during the addition
  2. temperatureThe mixture was then refluxed for 1 hour
  3. temperaturecooled to 50° C
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customdried at 50° C. to constant weight

Sources & evidence

ORD record
ord-5493d8db536545a9965448abed8c6541
Source dataset
uspto-grants-2003_12
Patent number
US06660773B2

Reaction notes

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