4-Chloro-8-(trifluoromethyl)quinoline → dimethylphosphinyl-methyl N-(8-trifluoromethyl-4-quinolyl)-anthranilate

HRID 971619

Reaction equation

HRID 971619 reaction equation
[C:1]([O:10][CH2:11][P:12]([CH3:15])([CH3:14])=[O:13])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl[C:17]1[C:26]2[C:21](=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1>C(O)(C)C.Cl>[F:30][C:27]([F:28])([F:29])[C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:21]=1[N:20]=[CH:19][CH:18]=[C:17]2[NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([O:10][CH2:11][P:12]([CH3:15])([CH3:14])=[O:13])=[O:9]

Participants

5

Reactant 2

HCID 902624-Chloro-8-(trifluoromethyl)quinolineHCID 12669155Dimethylphosphinylmethyl anthranilate

Product 1

HCID 12669152dimethylphosphinyl-methyl N-(8-trifluoromethyl-4-quinolyl)-anthranilate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

4.6 grams (0.02 mol) of dimethylphosphinylmethyl anthranilate and 4.6 grams (0.02 mol) of 4-chloro-8-trifluoromethylquinoline are kept at 80° C. for about three and a half hours in 15 ml of isopropanol and 2.3 ml of concentrated aqueous hydrochloric acid. After removing the solvents and excess hydrochloric acid, the free base of the ester is liberated at 0° C. The dimethylphosphinyl-methyl N-(8-trifluoromethyl-4-quinolyl)-anthranilate obtained is identical to that prepared in Example 2a). Yield: 7.6 grams (90% of theory).

Workup

  1. customAfter removing the solvents and excess hydrochloric acid
  2. customis liberated at 0° C

Sources & evidence

ORD record
ord-b80cd8f233344c97a8eee27789d951d4
Source dataset
uspto-grants-1979_07
Patent number
US04160828

Linked notes

Loading…