Hydrochloric Acid → 4-[(7-Chloroquinolin-4-yl)amino]benzoic acid

HRID 1586971Notes

Reaction equation

HRID 1586971 reaction equation
Cl.C[O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.Cl>[OH-].[K+].O>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([NH:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:23])=[O:3])=[CH:10][CH:9]=3)=[CH:13][CH:14]=[N:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 678596174-[(7-Chloro-4-quinolinyl)amino]benzoic acid methyl ester hydrochloride

Product 1

HCID 6862834-[(7-Chloroquinolin-4-yl)amino]benzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

4-[(7-Chloro-4-quinolinyl)amino]benzoic acid methyl ester hydrochloride (15.0 g, 43.0 mmol) is stirred in 150 mL of 1N KOH (aq) and refluxed for 1.5 hours, over which time the material dissolves. The hot solution is then poured into a 1 L Erlenmeyer flask containing a stirring solution of 107 mL of 1N HCl (aq) in 500 mL of water. A yellow solid forms immediately and the mixture is allowed to cool to room temperature. The solid is filtered and washed with cold methanol and ether, and allowed to air dry in the funnel, to afford 9.31 g (31.2 mmol, 73% yield) of product as a pale yellow solid: 1H NMR (Me2SO-d6, 300 MHz) δ12.6 (br s, 1H) 9.4 (br s, 1H), 8.58 (d, J=5.4 Hz, 1H), 8.40 (d, J=9.0 Hz, 1H), 7.94 (m, 3H), 7.6 (d of d, J=2.1, 9.3 Hz, 1H), 7.4 (d, J=8.7 Hz, 2H) 7.2 (d, J=5.6 Hz, 1H).

Workup

  1. temperaturerefluxed for 1.5 hours, over which time the material
  2. dissolutiondissolves
  3. additionThe hot solution is then poured into a 1 L Erlenmeyer flask
  4. filtrationThe solid is filtered
  5. washwashed with cold methanol and ether
  6. customto air dry in the funnel

Sources & evidence

ORD record
ord-2596da03fdab495aa37bacd71b70f222
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

Loading…