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

HRID 1354599ノート

反応式

HRID 1354599 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, 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.).

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

出典と根拠

ORDレコード
ord-23ea37c6bc7e46c9b8f62b629dc5832d
出典データセット
uspto-grants-2007_05
特許番号
US07223757B2

反応ノート

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