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

HRID 613599ノート

反応式

HRID 613599 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 104895412-amino-3-benzyloxy-N-methylaniline収率 87.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-89e3579cf22a4c9680c702153096afa2
出典データセット
uspto-grants-1999_12
特許番号
US06008229

反応ノート

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