Pyridine → HCID 18645505, compound

HRID 1885327Notes

Reaction equation

HRID 1885327 reaction equation
[C:1]([NH:4][NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:27](Cl)(=[O:29])[CH3:28]>C(Cl)(Cl)Cl>[C:27]([N:5]([C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])[NH:4][C:1](=[O:3])[CH3:2])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18645506HCID 18645506, compound

Product 1

HCID 18645505HCID 18645505, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

Trans-4-(2-acetylhydrazino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol, 320 mg, was dissolved in 6 ml of chloroform and to this was added 0.5 ml of pyridine. While stirring under water cooling (20° C.), 0.23 ml of acetyl chloride was added and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off under a reduced pressure, and to the residue was added ice water to scrape and crush it. After filtration and drying, it was recrystallized from ethyl acetate - hexane (1:1) to give 260 mg of trans-4-(1,2-diacetylhydrazino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol as white crystals, m.p. 230°-233° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. distillationThe solvent was distilled off under a reduced pressure
  3. additionto the residue was added ice water
  4. customcrush it
  5. filtrationAfter filtration
  6. customdrying
  7. customit was recrystallized from ethyl acetate - hexane (1:1)

Sources & evidence

ORD record
ord-d737f1a3885247b6879d832c08f0c7fb
Source dataset
uspto-grants-1992_09
Patent number
US05143936

Reaction notes

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