HCID 53964573, compound → HCID 13580002, compound

HRID 482894Notes

Reaction equation

HRID 482894 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]2[C:10](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]2[CH:10]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 53964573HCID 53964573, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13580002HCID 13580002, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinecarboxylic acid ethyl ester (3.4 g) in ethyl acetate (150 ml) is treated with 10 percent palladium on carbon (0.70 g) and reduced at 40 p.s.i. hydrogen pressure for 3 hours. Catalyst is filtered and the filtrate is evaporated to yield 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethyl)-3-quinolinecarboxylic acid ethyl ester (3.28 g) as an oil.

Workup

  1. filtrationCatalyst is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-5718ec806a224812b04a045c1a349ea2
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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