6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine → 1,2,3,4-tetrahydro-N3,N3-dipropyl-3,8-quinolinediamine

HRID 327463Notes

Reaction equation

HRID 327463 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[NH:8][CH2:7][CH:6]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:5]2>C(O)C.[Pd]>[CH2:19]([N:15]([CH2:16][CH2:17][CH3:18])[CH:6]1[CH2:5][C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=[CH:2][CH:3]=2)[NH:8][CH2:7]1)[CH2:20][CH3:21]

Participants

4

Reactant 1

HCID 199194006-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine

Product 1

HCID 152919501,2,3,4-tetrahydro-N3,N3-dipropyl-3,8-quinolinediamineYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine (2.7 g) and 10% palladium charcoal (0.5 g) in ethanol (150 mL) was hydrogenated for 18 hours. The solution was filtered and the ethanol evaporated to give 1.9 g of 1,2,3,4-tetrahydro-N3,N3 -dipropyl-3,8-quinolinediamine as an oil.

Workup

  1. filtrationThe solution was filtered
  2. customthe ethanol evaporated

Sources & evidence

ORD record
ord-5096e36bf38d40bdada1cdf61f0a090e
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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