HCID 10036479, compound → 6-Amino-1,2,3,4-tetrahydroquinoline-8-carboxylic acid

HRID 1885870Notes

Reaction equation

HRID 1885870 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]([OH:16])=[O:15])[CH:13]=1)[NH:10][CH2:9][CH2:8][CH2:7]2)([O-])=O>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]([OH:16])=[O:15])[CH:13]=1)[NH:10][CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 10036479HCID 10036479, compound

Product 1

HCID 149884736-Amino-1,2,3,4-tetrahydroquinoline-8-carboxylic acidYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-nitro-1,2,3,4-tetrahydroquinoline-8-carboxylic acid (4.5 g) in DMF (200 ml) was hydrogenated in the presence of 10% palladium on charcoal (1 g) for 5 hours. After removal of the catalyst by filtration, solvent was distilled away to give the title compound (3.72 g, 96.8%). This compound was recrystallized from DMF-ethanol to give brown crystals, mp 207°-208° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration, solvent
  3. distillationwas distilled away

Sources & evidence

ORD record
ord-dc3713e39e274fd68b8d6053ccb7cf83
Source dataset
uspto-grants-1992_09
Patent number
US05147874

Reaction notes

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