Hydrochloric Acid → 8-Methoxy-4-[(2-methylphenyl)amino]-3-quinolinecarboxylic Acid

HRID 66776Notes

Reaction equation

HRID 66776 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]CC)=[O:14])=[C:8]2[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25].[OH-].[Na+].C(O)C.Cl>O>[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]([OH:15])=[O:14])=[C:8]2[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 130384398-Methoxy-4-o-tolylamino-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 130384408-Methoxy-4-[(2-methylphenyl)amino]-3-quinolinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Ethyl 8-methoxy-4-[(2-methylphenyl)amino]-3-quinolinecarboxylate, 15.00 g (0.0445 mole), 100 ml of 3 N sodium hydroxide solution and 100 ml of ethanol was stirred at room temperature for 16 hours. The mixture was diluted with 300 ml of water and acidified to pH 6.8 with 6 N hydrochloric acid solution. The precipitate was collected by filtration, washed in succession with water and acetone and air dried for about 1.5 hr. Weight of solid was 13.41 g (98%), m.p. 272° C. (d).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed in succession with water and acetone and air
  3. customdried for about 1.5 hr

Sources & evidence

ORD record
ord-01be616c14cc409ba37998d98552c46b
Source dataset
uspto-grants-1982_08
Patent number
US04343804

Reaction notes

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