HCID 54439984, compound → HCID 24845782, compound

HRID 615403Notes

Reaction equation

HRID 615403 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18](O)=[O:19])[CH:9]=1>S(Cl)(Cl)=O>[CH3:12][N:11]([CH:10]([CH3:18])[CH2:9][CH3:8])[C:18]([C:10]1[CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)=[O:19]

Participants

3

Reactant 1

HCID 54439984HCID 54439984, compound

Product 1

HCID 24845782HCID 24845782, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

3.3 g of 4-(2-fluorophenyl) quinoline 2-carboxylic acid in 10 ml of thionyl chloride are brought to boiling point. After reaction, the thionyl chloride is evaporated and the residue taken up in 30 ml of toluene which is again evaporated. The residue is redissolved in 100 ml of toluene and 4.8 ml of triethylamine, then under agitation, 1.8 g of N-methyl 2-butanamine hydrochloride are added. After 14 h. the reaction mixture is taken up in 100 ml of water. The organic phase is decanted, the aqueous phase is extracted 3 times each with 100 ml of ether. The organic phases are washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel using a cyclohexane/ethylacetate (70:30) mixture as eluant. After recrystallization in isopropylether/ether (5:2) mixture, 1.16 g of N-methyl N-(1-methylpropyl) 4-(2-fluorophenyl) quinoline 2-carboxamide melting at 86° C. is obtained.

Workup

  1. customAfter reaction
  2. customthe thionyl chloride is evaporated
  3. customis again evaporated
  4. dissolutionThe residue is redissolved in 100 ml of toluene
  5. addition4.8 ml of triethylamine, then under agitation, 1.8 g of N-methyl 2-butanamine hydrochloride are added
  6. customThe organic phase is decanted
  7. extractionthe aqueous phase is extracted 3 times each with 100 ml of ether
  8. washThe organic phases are washed with water
  9. dry with materialdried over magnesium sulphate
  10. customevaporated under reduced pressure
  11. customThe residue is chromatographed on silica gel using a cyclohexane/ethylacetate (70:30) mixture as eluant
  12. customAfter recrystallization in isopropylether/ether (5:2) mixture

Sources & evidence

ORD record
ord-67500734c1e14801850bce0f6d2df9e1
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Reaction notes

Loading…