4-Imidazol-1-yl-2-methyl-6-nitro-phenylamine → 5-Imidazol-1-yl-3-methyl-benzene-1,2-diamine

HRID 1767006Notes

Reaction equation

HRID 1767006 reaction equation
[N:1]1([C:6]2[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([NH2:15])=[C:8]([CH3:16])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>[Pd].O>[N:1]1([C:6]2[CH:11]=[C:10]([NH2:12])[C:9]([NH2:15])=[C:8]([CH3:16])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 220210264-Imidazol-1-yl-2-methyl-6-nitro-phenylamine

Product 1

HCID 104199825-Imidazol-1-yl-3-methyl-benzene-1,2-diamineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To 4-imidazol-1-yl-2-methyl-6-nitro-phenylamine (350 mg, 1.61 mmol) and 10% Palladium on carbon (40 mg) were added degassed methanol (5 mL) and TFA (5 drops). The reaction mixture was flushed and evacuated with hydrogen/vacuum line, stirred at room temperature for 14 h under hydrogen atmosphere (hydrogen balloon). The dark reaction mixture was filtered through a pad of celite and rinsed with methanol. Concentration of the filtrate gave the residue, which was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4. Concentration to dryness gave the title compound (275 mg, 91%) as a solid. 1H NMR (300 MHz, CD3OD) δ 7.87 (1H, s), 7.34 (1H, s), 7.05 (1H, s), 6.72 (1H, d, J=2.4 Hz), 6.65 (1H, d, J=2.4 Hz) 2.21 (3H, s). LCMS (M+H)+ m/z 189 (t=0.23 min.).

Workup

  1. customdegassed methanol (5 mL) and TFA (5 drops)
  2. customThe reaction mixture was flushed
  3. customevacuated with hydrogen/vacuum line
  4. customThe dark reaction mixture
  5. filtrationwas filtered through a pad of celite
  6. washrinsed with methanol
  7. customConcentration of the filtrate gave the residue, which
  8. extractionextracted with ethyl acetate
  9. washThe combined organic layers were washed with saturated NaHCO3, brine
  10. dry with materialdried over Na2SO4
  11. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-4277d066ca04415d899a16537ec3df22
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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