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

HRID 2281896노트

반응식

HRID 2281896 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 247289115-bromo-1H-indazole-3-carbonitrile수율 60.6%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

반응 조건

온도
-50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-37aec6c33f4f462c91c543cffc0329f8
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139587B2

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