Hydrochloric Acid → p-[(7-trifluoromethyl-4-quinolyl)amino]-N,N-dimethylbenzamide

HRID 2398726Notes

Reaction equation

HRID 2398726 reaction equation
[CH3:1][N:2]([CH3:12])[C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1.Cl.[OH-].[Na+]>C(O)C>[F:27][C:24]([F:25])([F:26])[C:20]1[CH:19]=[C:18]2[C:23]([C:14]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([N:2]([CH3:12])[CH3:1])=[O:11])=[CH:5][CH:6]=3)=[CH:15][CH:16]=[N:17]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 2355274-Amino-N,N-dimethylbenzamide

Product 1

HCID 21433867p-[(7-trifluoromethyl-4-quinolyl)amino]-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.1 mole of N,N-dimethyl-p-aminobenzamide, 0.1 mole of 4-chloro-7-trifluoromethylquinoline, 8 ml. of concentrated hydrochloric acid and 500 ml. of absolute ethanol is heated at reflux for 19 hours, after which 100 ml. of 2.5N sodium hydroxide is added. The mixture is cooled and filtered and the filter cake is recrystallized from methanol. There is thus obtained p-[(7-trifluoromethyl-4-quinolyl)amino]-N,N-dimethylbenzamide.

Workup

  1. temperatureat reflux for 19 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customthe filter cake is recrystallized from methanol

Sources & evidence

ORD record
ord-571c6d3402fc4c39a9d1a70b7c14419a
Source dataset
uspto-grants-1977_05
Patent number
US04025629

Reaction notes

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