5-(2-Methylmorpholino)-2-nitroaniline → 4-(2-Methylmorpholino)benzene-1,2-diamine

HRID 1047570ノート

反応式

HRID 1047570 の反応式
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-])=O)=[C:12]([CH:14]=2)[NH2:13])[CH2:5][CH2:4][O:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[CH:14]=[C:12]([NH2:13])[C:11]([NH2:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1

参加物

5

反応物 2

HCID 683849655-(2-Methylmorpholino)-2-nitroanilineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 683850274-(2-Methylmorpholino)benzene-1,2-diamine収率 85.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

5-(2-Methylmorpholino)-2-nitroaniline (200 mg, 0.843 mmol) was added to the 10% Pd/C (25 mg) in ethanol (25 mL) and then hydrogen gas (60 psi) was applied for overnight at room temperature. The reaction mixture was filtered through Celite, and the solvent was removed in vacuo. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (150 mg). 1H NMR: (400 MHz, DMSO-d6): δ 6.38 (d, 1H, J=8.0 Hz), 6.18 (d, 1H, J=2.4 Hz), 5.99 (dd, 1H, J=2.8 and 8.0 Hz), 4.34 (bs, 2H), 3.96 (bs, 2H), 3.82 (m, 1H), 3.57 (m, 2H), 3.19 (d, 1H, J=11.2 Hz), 3.11 (d, 1H, J=11.2 Hz), 2.44 (m, 1H), 2.13 (t, 1H, J=11.2 Hz), 1.08 (d, 3H, J=6.4 Hz).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

出典と根拠

ORDレコード
ord-a886b3a13f8e4764a3ed840d6978e756
出典データセット
uspto-grants-2013_10
特許番号
US08569511B2

反応ノート

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