Hydrazine → HCID 14698017、化合物

HRID 1023892ノート

反応式

HRID 1023892 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:14][CH:13]=[N:12][CH:11]=1)([O-])=O.NN>CO>[NH:14]1[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])=[CH:11][N:12]=[CH:13]1

参加物

4

反応物 2

HCID 9321HydrazineHCID 135528715-(2-Nitrophenyl)-1H-imidazole

生成物 1

HCID 14698017HCID 14698017、化合物収率 26%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a vial were added 5-(2-nitrophenyl)-1H-imidazole (200 mg, 1.06 mmol), ferric chloride (8.6 mg, 0.35 mmol), activated carbon (2.2 mg, 1.80 mmol) and hydrazine (1.1 ml, 21.2 mmol) and methanol (9 mL). The resulting mixture was stirred at r.t. for 5 min then was heated to 70° C. for two days. The reaction was cooled to room temperature and filtered. The filtrate was concentrated and purified to give 2-(1H-imidazol-5-yl)aniline. The intermediate was dissolved in acetic acid (2 ml) and formaldehyde (37% in water, 0.3 ml) was added. The reaction was stirred for 1 h at room temperature, diluted with 30 ml ethyl acetate, and extracted with 5% HCl. The aqueous layer was basified with K2CO3 (add gradually until PH=7), then extracted with ethyl acetate (30 mL*2). The organic layer was evaporated under reduced pressure and product was obtained by column chromatography using ethyl acetate as eluent (26% yield). 1H NMR: 4.70 (s, 1H), 4.93 (s, 2H), 7.50-7.56 (m, 1H), 7.73-7.82 (m, 3H), 8.24-8.31 (m, 2H).

後処理

  1. temperaturethen was heated to 70° C. for two days
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified

出典と根拠

ORDレコード
ord-e5941c7715084b7ab513f2efb40c6fbf
出典データセット
uspto-grants-2014_05
特許番号
US08722720B2

反応ノート

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