4-Amino-2,5-dimethylbenzonitrile → 6-Methyl-1H-indazole-5-carbonitrile

HRID 2228738노트

반응식

HRID 2228738 반응식
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:11])[CH:3]=1.[N:12]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:11][C:4]1[CH:3]=[C:2]2[C:9]([CH:10]=[N:12][NH:1]2)=[CH:8][C:5]=1[C:6]#[N:7]

참가 물질

5

반응물 2

HCID 184708764-Amino-2,5-dimethylbenzonitrileHCID 23668193Sodium Nitrite

생성물 1

HCID 184708486-Methyl-1H-indazole-5-carbonitrile수율 21%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+.

후처리

  1. waitthen left
  2. customThe solvent was removed by evaporation
  3. customthe residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-eaa59e39291f4f89a772656e85ac558e
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417203B1

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