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

HRID 1697442노트

반응식

HRID 1697442 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 12571735o-(4-Chlorophenyl)hydroxylamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d5b0d20dac0849c6ae4cb41d7105fad4
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163915B2

반응 노트

불러오는 중…