Hydrochloric Acid → 2-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

HRID 484786Notes

Reaction equation

HRID 484786 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1.[ClH:17]>C(O)C.[Pd]>[ClH:17].[ClH:17].[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13520142N-(2-Methyl-4-nitrophenyl)-3,4-dihydro-2H-pyrrol-5-amine

Product 1

HCID 1317142942-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product compound of Example 8 was dissolved in 1.2 liter of ethanol containing 53.4 ml of concentrated hydrochloric acid and hydrogenated at 2 psi over 5% palladium on carbon. After removal of catalyst by filtration, the filtrate was concentrated in vacuo to give 85 g of the title compound. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7b907801ad1e442e9344b86ae0bea55e
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

Loading…