Ethanol → HCID 86752615, compound

HRID 1292069Notes

Reaction equation

HRID 1292069 reaction equation
[CH3:1][C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[C:5](=[O:15])[NH:4][N:3]=1.O.C(O)C.S(=O)(=O)(O)O>[Pd].C(O)(=O)C>[CH3:1][C:2]1[C:14]2[N:13]3[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)=[CH:7][C:6]=2[C:5](=[O:15])[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 157133114-methyl-2H-pyridazino[4,5-b]indolizine-1-one

Product 1

HCID 86752615HCID 86752615, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4-Methylpyridazino[4,5-b]indolizin-1-one (5.08 g, 25.5 mmol) was hydrogenated at room temperature and 55 psi using a Parr apparatus in a mixture containing 100 mL each of water, ethanol and acetic acid, 3 mL of concentrated sulfuric acid, and 10% Pd on charcoal (500 mg). A white precipitate was observed. The precipitate and catalyst were filtered through Solka Floc and the solids were washed with methanol and methylene chloride. The washes were evaporated to give 6,7,8,9-tetrahydro-4-(methyl)pyridazino[4,5-b]indolizin-1-one (XI). The reduction filtrate was evaporated in vacuo to remove most of the volatiles, then filtered to isolate additional XI. The aqueous phase was then washed with methylene chloride to extract the remaining XI. The product from all three fractions was combined and dried in vacuo to give 3.2 g (67%) of XI.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe precipitate and catalyst were filtered through Solka Floc
  3. washthe solids were washed with methanol and methylene chloride
  4. customThe washes were evaporated

Sources & evidence

ORD record
ord-070493017eb640598261d9eabad26bb1
Source dataset
uspto-grants-1998_05
Patent number
US05756501

Reaction notes

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