3-nitro-5,6,7,8-tetrahydroquinoline → 5,6,7,8-tetrahydroquinolin-3-amine

HRID 1768754Notes

Reaction equation

HRID 1768754 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-])=O>CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

4

Reactant 1

HCID 110303733-nitro-5,6,7,8-tetrahydroquinoline

Product 1

HCID 106543695,6,7,8-tetrahydroquinolin-3-amineYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of 15.8 g of 3-nitro-5,6,7,8-tetrahydroquinoline [synthesized according to the method as described in Bull. Chem. Soc. Jpn. Vol. 63 (1990), 2820] and 1.6 g of 5% palladium carbon in 300 ml of methanol is hydrogenerated at ordinary temperature under atmospheric pressure. The catalyst is filtered off, and the filtrate is concentrated in vacuo to remove the solvent. The resultant crude product is recrystallized from methylene chloride-isopropyl ether to give 12.76 g of the titled compound 1. Yield: 97%

Workup

  1. customsynthesized
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in vacuo
  4. customto remove the solvent
  5. customThe resultant crude product is recrystallized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-c29840ef666e4471a41ec3482ef0cff0
Source dataset
uspto-grants-1995_01
Patent number
US05378848

Reaction notes

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