Hydrazine hydrate (1:1) → o-(4-Chlorophenyl)hydroxylamine

HRID 1697442ノート

反応式

HRID 1697442 の反応式
O.NN.[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][N:10]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1>C(Cl)(Cl)Cl.CO>[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][NH2:10])=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 153707352-(4-Chlorophenoxy)isoindoline-1,3-dione

生成物 1

HCID 12571735o-(4-Chlorophenyl)hydroxylamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

Hydrazine hydrate (0.56 mL, 12 mmol) was added to a solution of Example 3A (820 mg, 3.0 mmol) in chloroform (37 mL) and methanol (4 mL). The suspension was stirred at room temperature for 22 hours. Silica gel (10 g) was added, and the mixture was concentrated to dryness. The residue was applied to the top of a flash chromatography column and eluted with hexanes-ethyl acetate (80:20) to provide the title compound as the free amine. The residue was dissolved in ethanol (5 mL) and treated with HCl/dioxane (4M, 1 mL). The solution was heated at reflux and diluted with gradual addition of ethyl acetate (50 mL). The mixture was cooled to room temperature and filtered to provide the title compound as a hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 7.15-7.22 (m, 2 H), 7.42-7.49 (m, 2 H).

後処理

  1. additionSilica gel (10 g) was added
  2. concentrationthe mixture was concentrated to dryness
  3. washeluted with hexanes-ethyl acetate (80:20)

出典と根拠

ORDレコード
ord-d5b0d20dac0849c6ae4cb41d7105fad4
出典データセット
uspto-grants-2012_04
特許番号
US08163915B2

反応ノート

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