Methanol → HCID 15591007, compound

HRID 255645Notes

Reaction equation

HRID 255645 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:10]=[C:11]([C:15](=[O:17])[CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:29]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH:10]=[C:11]([C:15](=[O:17])[CH:16]=2)[C:12]([O:14][CH3:29])=[O:13])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 15591126HCID 15591126, compound

Product 1

HCID 15591007HCID 15591007, compound

Conditions

Temperature
5 °C

Procedure

In 50 ml of methanol was suspended 6.5 g of 6-(4-aminophenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinic acid, and the suspension was cooled to 5° C., after which 3.9 g of thionyl chloride was added dropwise thereto over 10 minutes. After completion of the dropwise addition, the resulting mixture was refluxed for 6 hours, and then cooled to room temperature, after which the solvent was removed by distillation under reduced pressure. To the residue were added 30 ml of water and 30 ml of chloroform, and the resulting mixture was adjusted to a pH of 7 with sodium hydrogencarbonate, after which the aqueous layer was separated, washed with 30 ml of a saturated aqueous solution of sodium chloride, and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystalline substance was washed with 50 ml of diethyl ether to obtain 6.7 g of methyl 6-(4-aminophenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 250° C. or more.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe resulting mixture was refluxed for 6 hours
  3. temperaturecooled to room temperature
  4. customafter which the solvent was removed by distillation under reduced pressure
  5. additionTo the residue were added 30 ml of water and 30 ml of chloroform
  6. customafter which the aqueous layer was separated
  7. washwashed with 30 ml of a saturated aqueous solution of sodium chloride
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. washThe resulting crystalline substance was washed with 50 ml of diethyl ether

Sources & evidence

ORD record
ord-1caaa66753c04688a337144a7799ca89
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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