Acetic Anhydride → HCID 54473243, compound

HRID 255649Notes

Reaction equation

HRID 255649 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([CH3:18])=[CH:16][C:15](=[O:19])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9]2)=[CH:4][CH:3]=1.O=C(C=CC)CC(OC)=O.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1.C(OC(=O)C)(=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([CH:18]=[CH:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[CH:16][C:15](=[O:19])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 103713-PyridinecarboxaldehydeHCID 20183848HCID 20183848, compoundHCID 53436836Methyl 3-oxohex-4-enoate

Product 1

HCID 54473243HCID 54473243, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the same manner as in Example 4, methyl 1-(4-fluorophenyl)-6-methyl-4-oxo-1,4-dihydronicotinate (m.p. 190°-195° C.) was prepared from methyl 3-oxo-4-hexenoate and 4-flouoroaniline, and 0.7 g of this ester was mixed with 0.32 g of nicotinaldehyde and 0.58 g of acetic anhydride, and they were refluxed for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 20 ml of water was added thereto, after which the mixture was successively extracted with three 40-ml portions of chloroform. The chloroform layer was washed with 50 ml of a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform) to obtain 0.496 g of methyl 1-(4-fluorophenyl)-6-[2-(pyridin-3-yl)ethenyl]-4-oxo-1,4-dihydronicotinate having a melting point of 201°-204° C.

Workup

  1. temperaturewere refluxed for 5 hours
  2. customAfter completion of the reaction
  3. extractionafter which the mixture was successively extracted with three 40-ml portions of chloroform
  4. washThe chloroform layer was washed with 50 ml of a saturated aqueous solution of sodium chloride
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform)

Sources & evidence

ORD record
ord-8135474a262745eba25fc4d8078ebb59
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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