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

HRID 2228738ノート

反応式

HRID 2228738 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 184708486-Methyl-1H-indazole-5-carbonitrile収率 21%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-eaa59e39291f4f89a772656e85ac558e
出典データセット
uspto-grants-2002_07
特許番号
US06417203B1

反応ノート

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