Acetohydrazide → HCID 18645506, compound

HRID 1108964Notes

Reaction equation

HRID 1108964 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-52b3c545a4bd4e0392dafa5aceda7e5f
Source dataset
uspto-grants-1994_06
Patent number
US05318969

Reaction notes

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