Hydrazine → HCID 178518896, compound

HRID 911191Notes

Reaction equation

HRID 911191 reaction equation
[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[C:14]([OH:16])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][NH2:18]>[NH4+].[Cl-].CCOC(C)=O>[C:2]1([C:1]2[C:9]3[CH:13]=[CH:12][O:11][C:10]=3[C:14]([OH:16])=[N:18][N:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 19382374HCID 19382374, compound

Product 1

HCID 178518896HCID 178518896, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A brown solution of 3-benzoylfuran-2-carboxylic acid (0.770 g, 3.56 mmol) and anhydrous hydrazine (0.568 ml, 17.8 mmol) was heated to 100° C. in a sealed tube for approx. 72 h. The reaction was cooled, and diluted with sat'd aq. NH4Cl and EtOAc. The organic layer was washed with sat'd aq. NH4Cl and brine, and dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 4-phenylfuro[3,2-d]pyridazin-7-ol which was carried on without further purification. MS m/z=213 [M+H]+. Calc'd for C12H8N2O2: 212.2.

Workup

  1. temperatureThe reaction was cooled
  2. washThe organic layer was washed with sat'd aq. NH4Cl and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a44a9aba3a6e4f2cb9247fb328dbfad0
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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