4-Amino-m-cresol → HCID 19880277, compound

HRID 1885176Notes

Reaction equation

HRID 1885176 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]2Cl.[OH:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([CH3:27])[CH:21]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]2[NH:24][C:23]1[CH:25]=[CH:26][C:20]([OH:19])=[CH:21][C:22]=1[CH3:27]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester

Product 1

HCID 19880277HCID 19880277, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 8-methoxy-4-chloroquinoline-3-carboxylate (2.6 g, 0.0098 mol) and 4-hydroxy-2-methylaniline (2.4 g, 0.0196 mol) in ethanol (150 ml) were heated under refulx for 30 minutes. The solvent was evaporated under reduced pressure. The residue was dissolved in chloroform and extracted with 2N hydrochloric acid (3×100 ml). On basification of the chloroform extracts, a solid precipitated out, this was collected by filtration and dried. Recrystallisation from dimethylformamide gave the title compound. Yield=2.52 g, m.p. 277°-279° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. extractionextracted with 2N hydrochloric acid (3×100 ml)
  4. customa solid precipitated out
  5. filtrationthis was collected by filtration
  6. customdried
  7. customRecrystallisation from dimethylformamide

Sources & evidence

ORD record
ord-9cbea1f0d06e491f9f93bf68941caea2
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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