Ethanol → HCID 12291079, compound

HRID 1579063Notes

Reaction equation

HRID 1579063 reaction equation
[O:1]1[C:5](=[O:6])[C:4](=O)[C:3]2[CH2:8][CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:2]1=2.Cl.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:26](O)[CH3:27]>>[C:18]1([N:24]2[C:2]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[CH2:10][CH2:9][CH2:8][C:3]=3[C:4]([C:5]([O:1][CH2:26][CH3:27])=[O:6])=[N:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 60962Phenylhydrazine hydrochlorideHCID 2404555,6-dihydro-2h-benzo[6,7]cyclohepta[1,2-b]furan-2,3(4h)-dione

Product 1

HCID 12291079HCID 12291079, compound

Procedure

A mixture of 25 parts of 5,6-dihydro-4H-benzo-[6,7]cyclohepta[1,2-b]furan-2,3-dione, 21 parts of phenylhydrazine hydrochloride and 400 parts of absolute ethanol are refluxed for 6 hours. The ethanol is then removed under reduced pressure and the resulting residue is partitioned between benzene and water with sufficient potassium carbonate being added to make the mixture alkaline. The organic layer is then separated and washed twice with water before it is dried over potassium carbonate and the solvent is evaporated under reduced pressure. The resulting residue is recrystallized from hexane to give ethyl 1-phenyl-1,4,5,6-tetrahydrobenzo-[6,7]cyclohepta[1,2-c]pyrazole-3-carboxylate melting at about 110°-111°C.

Workup

  1. temperatureare refluxed for 6 hours
  2. customThe ethanol is then removed under reduced pressure
  3. customthe resulting residue is partitioned between benzene and water with sufficient potassium carbonate being
  4. additionadded
  5. customThe organic layer is then separated
  6. washwashed twice with water before it
  7. dry with materialis dried over potassium carbonate
  8. customthe solvent is evaporated under reduced pressure
  9. customThe resulting residue is recrystallized from hexane

Sources & evidence

ORD record
ord-35229fa190a6465a8e78c00b99b455a9
Source dataset
uspto-grants-1976_02
Patent number
US03940418

Reaction notes

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