Pyridine → HCID 67876045, compound

HRID 1885329Notes

Reaction equation

HRID 1885329 reaction equation
[C:1]([NH:9][NH:10][C@@H:11]1[C:16]2[CH:17]=[C:18]([C:21]#[N:22])[CH:19]=[CH:20][C:15]=2[O:14][C:13]([CH3:24])([CH3:23])[C@H:12]1[OH:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)(Cl)Cl>[OH2:8].[C:32]([N:10]([C@@H:11]1[C:16]2[CH:17]=[C:18]([C:21]#[N:22])[CH:19]=[CH:20][C:15]=2[O:14][C:13]([CH3:23])([CH3:24])[C@H:12]1[OH:25])[NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 67842118HCID 67842118, compound

Product 1

HCID 67876045HCID 67876045, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trans-4-(2-benzoylhydrazino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol (320 mg) was dissolved in 1 ml of chloroform, 0.5 ml of pyridine was added, and 0.28 ml of acetyl chloride was added with stirring under ice cooling. After stirring at room temperature for 80 minutes, the solvent was distilled off under reduced pressure and the residue was dissolved in 5 ml of methanol. The solution was treated with 5 ml of 1N-sodium hydroxide at room temperature for 30 minutes. After the methanol had been distilled off, the residue was shaken together with ethyl acetate-water and the organic layer was washed with an aqueous solution of sodium chloride and subsequently concentrated. This was recrystallized from hexane-ethanol (1:1) to give 170 mg of trans-4-(1-acetyl-2-benzoylhydrazino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol monohydrate as white crystals, m.p. 212°-213° C.

Workup

  1. stirringAfter stirring at room temperature for 80 minutes
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 5 ml of methanol
  4. additionThe solution was treated with 5 ml of 1N-sodium hydroxide at room temperature for 30 minutes
  5. distillationAfter the methanol had been distilled off
  6. stirringthe residue was shaken together with ethyl acetate-water
  7. washthe organic layer was washed with an aqueous solution of sodium chloride
  8. concentrationsubsequently concentrated
  9. customThis was recrystallized from hexane-ethanol (1:1)

Sources & evidence

ORD record
ord-3f5ab62bad7d4cd18255c7735a34f09d
Source dataset
uspto-grants-1992_09
Patent number
US05143936

Reaction notes

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