Water → 4-[(4-chlorobenzyl)amino]benzoic acid

HRID 1902371Notes

Reaction equation

HRID 1902371 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 77264-Chlorobenzaldehyde

Product 1

HCID 39753974-[(4-chlorobenzyl)amino]benzoic acidYield 78%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

4-Aminobenzoic acid (13.7 g., 0.1 mole) and 4-chlorobenzaldehyde (14.05 g., 0.1 mole) were mixed in dry benzene (200 ml.), 4-toluenesulphonic acid (50 mg.) was added and the mixture was boiled under reflux in an apparatus incorporating a water-trap until the theoretical amount of water (1.8 ml) had been collected. The reaction mixture was cooled in iced water, the product filtered, dried and hydrogenated in NTP in ethanol (500 ml) in the presence of platinum oxide, (Adams catalyst), (100 mg). The catalyst was filtered off and the solution added to iced water. The product was filtered, dried and crystallised from 20% aqueous ethanol to give 4-[(4-chlorobenzyl)-amino]-benzoic acid (17.32 g., 78%) which melted at 206°-8° C.

Workup

  1. temperatureunder reflux in an apparatus
  2. customhad been collected
  3. temperatureThe reaction mixture was cooled in iced water
  4. filtrationthe product filtered
  5. customdried
  6. filtrationThe catalyst was filtered off
  7. additionthe solution added to iced water
  8. filtrationThe product was filtered
  9. customdried
  10. customcrystallised from 20% aqueous ethanol

Sources & evidence

ORD record
ord-313e88dc7368417993783434a3df6441
Source dataset
uspto-grants-1982_12
Patent number
US04362892

Reaction notes

Loading…