Water → N2,N4-Dibenzyl-6-trifluoromethyl-pyridine-2,3,4-triamine

HRID 639622Notes

Reaction equation

HRID 639622 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[C:11]([C:26]([F:29])([F:28])[F:27])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C1COCC1.CO.[Ni]>[CH2:1]([NH:8][C:9]1[C:14]([NH2:15])=[C:13]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=[C:11]([C:26]([F:29])([F:28])[F:27])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 962WaterHCID 67453795N2,N4-Dibenzyl-3-nitro-6-trifluoromethyl-pyridine-2,4-diamine

Product 1

HCID 67456850N2,N4-Dibenzyl-6-trifluoromethyl-pyridine-2,3,4-triamineYield 68%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

N2,N4-Dibenzyl-3-nitro-6-trifluoromethyl-pyridine-2,4-diamine (15.9 g, 35.6 mmol) was dissolved in a mixture of THF (100 ml) and MeOH (200 ml). Raney Nickel (3.18 g, 20 wt %) was added and the mixture was stirred at room temperature under 80 psi H2 for 1 hour. The mixture was filtered through celite to remove the catalyst and the filtrate was concentrated in vacuo to give an oil. Trituration in MeOH with a small amount of water gave a precipitate which was collected by filtration, washed with cold MeOH and dried in vacuo to give the title compound (9.02 g) as a white solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give an oil
  5. filtrationwas collected by filtration
  6. washwashed with cold MeOH
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d161a2bd9dbf416985b73b798edd4693
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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