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

HRID 1047570노트

반응식

HRID 1047570 반응식
[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

참가 물질

5

반응물 2

HCID 683849655-(2-Methylmorpholino)-2-nitroanilineHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a886b3a13f8e4764a3ed840d6978e756
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569511B2

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