Hydrazine hydrate (1:1) → 2-amino-3-benzyloxy-N-methylaniline

HRID 613599노트

반응식

HRID 613599 반응식
[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-])=O)=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[NH2:17][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=[CH:14][C:11]=1[NH:12][CH3:13]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 107298903-benzyloxy-2-nitro-N-methylaniline

생성물 1

HCID 104895412-amino-3-benzyloxy-N-methylaniline수율 87.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a mixture of 3-benzyloxy-N-methyl-2-nitroaniline (453.3 mg), 80% methanol (6.8 ml), anhydrous ferric chloride (13.6 mg) and carbon (13.6 mg) was dropwise added hydrazine monohydrate (255.6 μl) at 70° C., and the mixture was stirred for 5 hours at the same temperature. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. Ethyl acetate and saturated sodium bicarbonate solution were added to the residue, and the organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 2-amino-3-benzyloxy-N-methylaniline (348.9 mg). mp: 79-81° C., NMR (CDCl3, δ): 2.87 (3H, s), 3.43 (3H, br s), 5.07 (2H, s), 6.40 (1H, d, J=7.5 Hz), 6.49 (1H, d, J=7.5 Hz), 6.80 (1H, t, J=7.5 Hz), 7.29-7.47 (5H, m).

후처리

  1. customat 70° C.
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionEthyl acetate and saturated sodium bicarbonate solution were added to the residue
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

출처 및 근거

ORD 기록
ord-89e3579cf22a4c9680c702153096afa2
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008229

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