Ethanol → HCID 23019666, compound

HRID 1354187Notes

Reaction equation

HRID 1354187 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:7](=[O:24])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.[CH2:30](O)[CH3:31]>[H][H].[C].[Pd]>[CH:1]1([C:4]2[CH:5]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:7](=[O:24])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:30][CH3:31])[CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 702EthanolHCID 23019629HCID 23019629, compound

Product 1

HCID 23019666HCID 23019666, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

39 mg of ethyl 1-cyclopropyl-9-methyl-8-(3-nitrophenyl)-4-oxo-4H-quinolizine-3-carboxylate (Example 13) was dissolved in 2 ml of ethanol. 5 mg of 5% palladium carbon was added to the obtained solution, and they were stirred at room temperature in hydrogen atmosphere for 14 hours. The catalyst was taken by the filtration. Water was added to the filtrate. After the extraction with chloroform, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=100/1) to obtain 22 mg of ethyl 1-cyclopropyl-8-(3-ethylaminophenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. filtrationThe catalyst was taken by the filtration
  2. additionWater was added to the filtrate
  3. extractionAfter the extraction with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-0b49cdfc214049b88ef57352f4db7901
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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