1,2-Dichloropropane → N-(3'-trifluoromethylbenzoyl)-6-methylanthranilic acid

HRID 1902392Notes

Reaction equation

HRID 1902392 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](F)=[O:7].[CH3:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([NH2:24])[C:20]=1[C:21]([OH:23])=[O:22].C(N(CCCC)CCCC)CCC.ClCC(Cl)C>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:24][C:19]1[C:20](=[C:15]([CH3:14])[CH:16]=[CH:17][CH:18]=1)[C:21]([OH:23])=[O:22])=[O:7]

Participants

5

Reactant 4

HCID 65641,2-DichloropropaneHCID 7622TributylamineHCID 676063-(Trifluoromethyl)benzoyl fluorideHCID 1512106-Methylanthranilic acid

Product 1

HCID 12837110N-(3'-trifluoromethylbenzoyl)-6-methylanthranilic acid

Procedure

15.4 parts of 3-trifluoromethylbenzoyl fluoride are added to a stirred mixture of 13.3 parts of 6-methylanthranilic acid and 16.3 parts of tri-n-butylamine in 250 parts of 1,2-dichloropropane at 20°-25° C., and stirring is continued for 20 minutes. The precipitate formed is filtered off and washed with 1 N hydrochloric acid and then with water; the organic filtrate is washed similarly, dried and evaporated down. 27 parts of N-(3'-trifluoromethylbenzoyl)-6-methylanthranilic acid, of melting point 198°-204° C., are obtained.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with 1 N hydrochloric acid
  4. washthe organic filtrate is washed similarly
  5. customdried
  6. customevaporated down

Sources & evidence

ORD record
ord-44fa9780c72e4a19826273037b07e034
Source dataset
uspto-grants-1982_12
Patent number
US04363651

Reaction notes

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