Water → 2-(7-Chloro-4-quinolinylamino)-5-fluoro-benzoic acid

HRID 224587Notes

Reaction equation

HRID 224587 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=3[C:15]([O:17]C)=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=3[C:15]([OH:17])=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23331682Methyl 2-(7-chloro-4-quinolinylamino)-5-fluoro-benzoate

Product 1

HCID 233316862-(7-Chloro-4-quinolinylamino)-5-fluoro-benzoic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.8 g of the ester of Example 1, 25 ml of N sodium hydroxide solution, 25 ml of water and 100 ml of methanol was heated at 70°-75° C. for 90 minutes and the methanol was then evaporated. 100 ml of water and 10 ml of dimethylformamide were added to the mixture which was then heated to reflux. 4 ml of acetic acid were added thereto and the mixture was held in an ice bath for an hour and was then vacuum filtered. The recovered crystals were washed with water and dried to obtain 1.715 g of 2-(7-chloro-4-quinolinylamino)-5-fluoro-benzoic acid melting at 341°-342° C.

Workup

  1. customthe methanol was then evaporated
  2. addition100 ml of water and 10 ml of dimethylformamide were added to the mixture which
  3. temperaturewas then heated to reflux
  4. addition4 ml of acetic acid were added
  5. waitthe mixture was held in an ice bath for an hour
  6. filtrationvacuum filtered
  7. washThe recovered crystals were washed with water
  8. customdried

Sources & evidence

ORD record
ord-688202f6158442129ddb04a5b7e6061c
Source dataset
uspto-grants-1980_11
Patent number
US04233305

Reaction notes

Loading…