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

HRID 2210888Notes

Reaction equation

HRID 2210888 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% mp.: 97° to 98° C.

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-c1080f1dd6244c8fb91f1f9382e55657
Source dataset
uspto-grants-1995_10
Patent number
US05461062

Reaction notes

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