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

HRID 716824ノート

反応式

HRID 716824 の反応式
[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

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)2 回HCID 710901375-[(4-Nitrophenyl)oxy]-1,3-dihydro-2-benzofuran2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 702Ethanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-69df83a1bb95442f9472e7a3ade9155f
出典データセット
uspto-grants-2015_11
特許番号
US09193704B2

反応ノート

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