HCID 13143783, compound → HCID 13143782, compound

HRID 242893Notes

Reaction equation

HRID 242893 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>CCOC(C)=O>[C:12]1([CH3:17])[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 1

HCID 13143783HCID 13143783, compound

Product 1

HCID 13143782HCID 13143782, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3-nitropyridin-2-yl)-o-tolylamine (3.96 g, 17.3 mmol) in EtOAc (200 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (700 mg) and was stirred at RT under a hydrogen atmosphere for 16 h. The suspension was filtered and the filtrate was concentrated in vacuo to afford the title compound as a white solid (2.02 g, 59%). 1H NMR (CDCl3, 400 MHz): δ 7.83 (1H, d, J=4.94 Hz), 7.28-7.11 (3H, m), 7.01 (1H, d, J=7.64 Hz), 6.93 (1H, t, J=7.41 Hz), 6.79 (1H, dd, J=7.63, 4.96 Hz), 5.97 (1H, s), 3.43 (2H, s), 2.30 (3H, s).

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (700 mg)
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-146f27563a994f00aec27f3965bd25b6
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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