Acetohydrazide → HCID 18645506, compound

HRID 1885323Notes

Reaction equation

HRID 1885323 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]3[O:14][CH:8]3[C:7]=2[CH:15]=1)#[N:2].[C:16]([NH:19][NH2:20])(=[O:18])[CH3:17]>C(O)C>[C:16]([NH:19][NH:20][C@@H:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[C@H:9]1[OH:14])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 18645506HCID 18645506, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (5.0 g) and 4.0 g of acetohydrazide were dissolved in 20 ml of ethanol and the solution was heated under reflux for 9 hours. After the reaction, the ethanol was distilled off under reduced pressure and the residue was crushed by adding ice water and filtered to obtain crystals. The crystals were dried and recrystallized from ethyl acetate-ethanol (7:1) to give 5.3 g of trans-4-(2-acetylhydrazino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H 1-benzopyran-3-ol as white crystals, m.p. 209°-210° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 9 hours
  3. customAfter the reaction
  4. distillationthe ethanol was distilled off under reduced pressure
  5. customthe residue was crushed
  6. additionby adding ice water
  7. filtrationfiltered
  8. customto obtain crystals
  9. customThe crystals were dried
  10. customrecrystallized from ethyl acetate-ethanol (7:1)

Sources & evidence

ORD record
ord-eb4b08f005f94627ba3b3a8625b301f0
Source dataset
uspto-grants-1992_09
Patent number
US05143936

Reaction notes

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