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

HRID 372453

Reaction equation

HRID 372453 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 31/2 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. customare kept at 80° C for about 31
  2. customAfter removing the solvents and excess hydrochloric acid
  3. customis liberated at 0° C

Sources & evidence

ORD record
ord-73834c741bfc439da9a72fcec4cc69fd
Source dataset
uspto-grants-1978_05
Patent number
US04091095

Linked notes

Loading…