Hydrazine hydrate (1:1) → HCID 2810177, compound

HRID 564753Notes

Reaction equation

HRID 564753 reaction equation
C([O:3][C:4]([C:6]1[C:11]2=[CH:12][S:13][C:14]([NH2:15])=[C:10]2[C:9](=[O:16])[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1)=O)C.O.[NH2:24][NH2:25]>C(O)C>[NH2:15][C:14]1[S:13][CH:12]=[C:11]2[C:10]=1[C:9](=[O:16])[N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:7]=[C:6]2[C:4]([NH:24][NH2:25])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)3×HCID 647821HCID 647821, compound

Product 1

HCID 2810177HCID 2810177, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-Amino-4-oxo-3-phenyl-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester (20 g, 0.063 mol, prepared as described in example 25) in ethanol (400 ml) was added hydrazine hydrate (3.3 g, 0.066 mol). The reaction mixture was stirred at reflux temperature for 6 h at which time an additional portion of hydrazine hydrate (3.3 g, 0.066 mol) was added and the resulting mixture was stirred for an additional 66 h at reflux temperature. An additional portion of hydrazine hydrate (1.5 g, 0.03 mol) was added and the reaction mixture was stirred for an additional 16 h at reflux temperature. The reaction mixture was cooled and the precipitated was filtered off, washed with small portions of ethanol and dried in vacuo at 50° C. for 18 h which afforded 17.9 g (94%) of the title compound as a solid.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred for an additional 66 h
  3. temperatureat reflux temperature
  4. stirringthe reaction mixture was stirred for an additional 16 h
  5. temperatureat reflux temperature
  6. temperatureThe reaction mixture was cooled
  7. filtrationthe precipitated was filtered off
  8. washwashed with small portions of ethanol
  9. customdried in vacuo at 50° C. for 18 h which

Sources & evidence

ORD record
ord-823e4d0c7d62433e93afad0d2ef5f81f
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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