Formic Acid → N-(4-Methoxyphenyl)formamide

HRID 1448752Notes

Reaction equation

HRID 1448752 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:10](O)=[O:11]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]=[O:11])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 7732P-Anisidine

Product 1

HCID 79616N-(4-Methoxyphenyl)formamide

Conditions

Temperature
5 °C

Procedure

The intermediate, 4-methoxy formanilide is prepared by heating 369.6 parts by weight (3.0 mole) of para anisidine to 90° C. and adding to it 147 parts by weight (3.1 mole) of 97% formic acid over a period of 80 minutes at 95°-105° C. under reflux conditions. A water trap is then installed and heating continued at 91°-111° C. for about 5 hours while collecting water. Toluene is added to aid the removal of water. The reaction mixture is cooled, crystallization induced by scratching, and heptane added. The crystalline mass is cooled to 5° C. and filtered to obtain, after air drying 447.6 parts by weight of 4-methoxy formanilide as a purple solid.

Workup

  1. customA water trap is then installed
  2. temperatureheating
  3. customwhile collecting water
  4. additionToluene is added
  5. customthe removal of water
  6. temperatureThe reaction mixture is cooled
  7. customcrystallization
  8. additionheptane added
  9. filtrationfiltered
  10. customto obtain
  11. dry with materialafter air drying 447.6 parts by weight of 4-methoxy formanilide as a purple solid

Sources & evidence

ORD record
ord-5a982f963f7d49e4b68469e92d53b334
Source dataset
uspto-grants-1980_02
Patent number
US04187248

Reaction notes

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