Hydrazine hydrate (1:1) → 4-(1,3-Dihydro-2-benzofuran-5-yloxy)aniline

HRID 716824노트

반응식

HRID 716824 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:19]=[CH:18][C:14]3[CH2:15][O:16][CH2:17][C:13]=3[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Pd]>[CH2:15]1[C:14]2[CH:18]=[CH:19][C:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)=[CH:12][C:13]=2[CH2:17][O:16]1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)2회HCID 710901375-[(4-Nitrophenyl)oxy]-1,3-dihydro-2-benzofuran2회

생성물 1

HCID 867157014-(1,3-Dihydro-2-benzofuran-5-yloxy)aniline수율 90.5%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 702Ethanol용매

실험 절차

A solution of 5-[(4-nitrophenyl)oxy]-1,3-dihydro-2-benzofuran (Intermediate 74, 190 mg, 0.739 mmol), hydrazine hydrate (0.046 ml, 1.477 mmol) and Pd/C (157 mg, 0.148 mmol) in ethanol (6 ml) was stirred under argon at 90° C. After 4.5 hours 0.2 equivalents of Pd/C and 2 equivalents of hydrazine hydrate were added. After 1 more hour, the reaction mixture was cooled to room temperature and then filtered over celite and washed with methanol. The organic phase was concentrated and the residue was purified by SCX to afford the title compound (152 mg).

후처리

  1. filtrationfiltered over celite
  2. washwashed with methanol
  3. concentrationThe organic phase was concentrated
  4. customthe residue was purified by SCX

출처 및 근거

ORD 기록
ord-69df83a1bb95442f9472e7a3ade9155f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193704B2

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