Ammonium Hydroxide → 5-bromo-1H-indazole-3-carbonitrile

HRID 2064252ノート

反応式

HRID 2064252 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[N:12]([O-])=O.[Na+].[OH-].[NH4+]>Cl.O>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][N:12]=[C:9]2[C:10]#[N:11]

参加物

6

反応物 3

HCID 14923Ammonium HydroxideHCID 23668193Sodium NitriteHCID 450370522-(2-Amino-5-bromophenyl)acetonitrile

生成物 1

HCID 247289115-bromo-1H-indazole-3-carbonitrile収率 60.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
-50 °C

実験手順

To a cooled solution of (2-amino-5-bromophenyl)acetonitrile (11 g, 52 mmol) in concentrated hydrochloric acid (110 mL) at −50° C., a solution of sodium nitrite (3.9 g, 57 mmol) in water (20 mL) was added slowly. After the addition, the mixture was stirred at −50° C. for 2 h. The mixture was neutralized with 33% ammonium hydroxide at 0° C. and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with saturated sodium chloride (100 mL), dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by column chromatography (100-200 mesh silica gel) using 10% ethyl acetate in petroleum ether as eluent to afford 5-bromo-3-cyanoindazole (7 g, 60%) as a solid. 1HNMR (CDCl3) δ ppm 10.7 (br, 1H), 8.1 (s, 1H), 7.64 (d, 1H), 7.5 (d, 1H).

後処理

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layers were washed with saturated sodium chloride (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by column chromatography (100-200 mesh silica gel)

出典と根拠

ORDレコード
ord-e1fc14ac836846e584f89864c5b502dd
出典データセット
uspto-grants-2012_10
特許番号
US08288405B2

反応ノート

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