Methyl iodide → 4-Methoxy-N-methyl-2-nitrobenzenamine

HRID 1048987ノート

反応式

HRID 1048987 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[H-].[Na+].[CH3:15]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH3:15])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 667934-Methoxy-2-nitroaniline

生成物 1

HCID 35543134-Methoxy-N-methyl-2-nitrobenzenamine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-methoxy-2-nitro-phenylamine (5.0 g, 0.029 mol) in DMF (25 ml) was added NaH (0.9 g, 0.035 mol) at 0° C. and stirred at that temperature for 30 min. Methyl iodide (2.17 ml, 0.035 mol) was added and the resulting solution was stirred at room temperature for 30 min. The reaction was quenched with ice-water and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the title compound (4-methoxy-2-nitro-phenyl)-methyl-amine as a red solid. C8H10N2O3; 1H NMR (400 MHz, CDCl3), δ: 8.00 (brs, 1H), 7.62 (d, J=2.4 Hz, 1H), 7.18 (dd,1=9.2 Hz, J2=2.0 Hz, 1H), 6.82 (d, J=9.6 Hz, 1H), 3.81 (d, J=14.8 Hz, 3H), 3.02 (s, 3H). MS (M+1): 183.1.

後処理

  1. stirringthe resulting solution was stirred at room temperature for 30 min
  2. customThe reaction was quenched with ice-water
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-6b9c3a64e1ca465fad46e2963325afa1
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

反応ノート

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