4,8-Dichloroquinoline → Methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate

HRID 224595Notes

Reaction equation

HRID 224595 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>Cl>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[NH:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 889734,8-DichloroquinolineHCID 2783401Methyl 2-amino-5-fluorobenzoate

Product 1

HCID 23331697Methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoateYield 37.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 11.88 g of 4,8 dichloroquinoline, 10.4 g of methyl 2-amino-5-fluoro-benzoate and 60 ml of 2 N hydrochloric acid was refluxed for 21/2 hours and was then cooled to ≃0° C. and vacuum filtered. The moist residue was dissolved in 125 ml of lukewarm methanol and triethylamine was added to the resulting solution to make the pH alkaline. The mixture stood overnight at room temperature and was vacuum filtered and the recovered product was washed with water and dried to obtain 8.3 g of raw product which was crystallized from methanol to obtain 7.39 g of methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate melting at 196° C.

Workup

  1. temperaturewas refluxed for 21/2 hours
  2. temperaturewas then cooled
  3. customto ≃0° C.
  4. filtrationvacuum filtered
  5. dissolutionThe moist residue was dissolved in 125 ml of lukewarm methanol
  6. additiontriethylamine was added to the resulting solution
  7. filtrationfiltered
  8. washthe recovered product was washed with water
  9. customdried
  10. customto obtain 8.3 g of raw product which
  11. customwas crystallized from methanol

Sources & evidence

ORD record
ord-8e8e86e7a4f64221afc1550ed08a30bf
Source dataset
uspto-grants-1980_11
Patent number
US04233305

Reaction notes

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