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

HRID 970342ノート

反応式

HRID 970342 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

実験手順

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, and extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3, and brine and 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.). Procedure for the Preparation of 3,4-diamino-5-methyl-benzonitrile

後処理

  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, and brine
  10. dry with materialdried over Na2SO4
  11. concentrationConcentration to dryness

出典と根拠

ORDレコード
ord-12ff0bfce9d84b5a93e5f3e6fa169d2e
出典データセット
uspto-grants-2007_12
特許番号
US07312215B2

反応ノート

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