4-Amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile → 3,4-Diamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile

HRID 2246430Notes

Reaction equation

HRID 2246430 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=2)[N:5]=[C:4]([C:21]#[N:22])[C:3]=1[N+:23]([O-])=O>[Pd].C(OCC)(=O)C>[NH2:23][C:3]1[C:4]([C:21]#[N:22])=[N:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[C:10]([C:17]([F:20])([F:18])[F:19])[CH:9]=2)=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 589381224-Amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile

Product 1

HCID 589381183,4-Diamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-pyridine-2-carbonitrileYield 54.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 4-amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile (5 g, 14.2 mmol) and 10% Pd-C (wet) (5 g) under nitrogen was added ethyl acetate (500 ml). The vessel was purged with hydrogen and stirred at room temperature for 1.5 h before filtration through a cellite pad followed by concentration under reduced pressure to afford 3,4-diamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (2.5 g). 1H NMR (DMSO): δ 8.02 (m, 2H), 7.31 (d, 1H), 7.14 (s, 1H), 6.1 (bs, 2H), 5.69 (bs, 2H), 4.25 (q, 2H), 1.35 (t, 3H). MS m/z 323.3 (M+1).

Workup

  1. customThe vessel was purged with hydrogen
  2. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-bddda8934a9e4e219758ab011505a897
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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