HCID 14850773, compound → HCID 14850774, compound

HRID 1164852Notes

Reaction equation

HRID 1164852 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([C:20]([NH2:22])=[O:21])[CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>[Pd].CO>[CH2:1]([O:3][P:4]([CH2:9][C@H:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C@@H:12]([C:20]([NH2:22])=[O:21])[CH2:11]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 14850773HCID 14850773, compound

Product 1

HCID 14850774HCID 14850774, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 500 mg of 4-(diethylphosphonomethyl)-quinoline-2-carboxamide and 1 g of 10% palladium on charcoal in 75 ml of methanol is hydrogenated at 3 atmospheres pressure for 24 hours, filtered and evaporated to dryness. Chromatography on silica gel using methanol/methylene chloride (1:10) as eluent yields cis-4-(diethylphosphonomethyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-6dfa454e44ac4f2d92661060dad164d9
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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