Acetic Anhydride → HCID 19813417, compound

HRID 467125Notes

Reaction equation

HRID 467125 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[CH:18])[CH:12]=2)[C:9]([C:19]([O:21][CH3:22])=[O:20])=[C:8]([CH3:23])[NH:7][C:6]=1[CH:24]=O)=[O:4].Cl.[NH2:27]O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:24]([C:6]1[NH:7][C:8]([CH3:23])=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[CH:18])[CH:12]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4])#[N:27]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19813415HCID 19813415, compound

Product 1

HCID 19813417HCID 19813417, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 16 ml of acetic acid was dissolved 1.87 g (5.5 mmol) of 3,5-dimethoxycarbonyl-2-formyl-1,4-dihydro-6-methyl-4-(3 -ethynylphenyl)pyridine obtained in Example 15. Thereto were added 0.45 g (6.5 mmol) of hydroxylamine hydrochloride and 0.67 g (8.2 mmol) of sodium acetate. The admixture was stirred for 2.5 hours at room temperature. Then 1.96 g (19.2 mmol) of acetic anhydride was added thereto, and the admixture was reacted for 1.5 hours at room temperature, further for 4 hours at 95°-100° C. After completing the reaction, the reaction solution was concentrated under reduced pressure, water was added to the residue. After neutralization of the reaction mixture with saturated solution of sodium hydrogencarbonate, the reaction mixture was extracted with ethyl acetate several times. The organic layer thereof was washed with water, dehydrated and concentrated. The residue was purified by subjecting to silica gel column chromatography [eluent: benzene-ethyl acetate (10 : 1)] and recrystallized from the mixture of ethyl acetate and n-hexane to give 1.2 g of the desired compound as yellow prism crystals (yield: 66.7%).

Workup

  1. customthe admixture was reacted for 1.5 hours at room temperature, further for 4 hours at 95°-100° C
  2. customthe reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionAfter neutralization of the reaction mixture with saturated solution of sodium hydrogencarbonate, the reaction mixture was extracted with ethyl acetate several times
  6. washThe organic layer thereof was washed with water
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customrecrystallized from the mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-a3e1eb2775f6455999a304de54718eeb
Source dataset
uspto-grants-1992_10
Patent number
US05158963

Reaction notes

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