HCID 13788331, compound → 1(2H)-Pyridazinecarboxylic acid, tetrahydro-, ethyl ester

HRID 1437278Notes

Reaction equation

HRID 1437278 reaction equation
[H][H].[CH3:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1C(OCC1C=CC=CC=1)=O)=[O:7]>C(O)C.[C].[Pd]>[CH2:4]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])[CH3:3]

Participants

5

Reactant 2

HCID 13788331HCID 13788331, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 30143771(2H)-Pyridazinecarboxylic acid, tetrahydro-, ethyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In a hydrogen atmosphere, 10% palladium-carbon (3.2 g) was added to the above-obtained 1,2,3,6-tetrahydropyridazine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester (32 g) in ethanol (100 mL), and the resultant mixture was stirred at 40° C. for 24 hours, and then cooled in air. The reaction mixture was filtered, and the solvent of the filtrate was removed under reduced pressure, and the residue was purified by distillation (boiling point 81° C./1 mmHg), to thereby give hexahydropyridazine-1-carboxylic acid ethyl ester as an oily product (5.96 g, yield from the 2 processes: 31.1%).

Workup

  1. temperaturecooled in air
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent of the filtrate was removed under reduced pressure
  4. distillationthe residue was purified by distillation (boiling point 81° C./1 mmHg)

Sources & evidence

ORD record
ord-0ea3fc8e76eb4e7a949910d3448d0311
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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