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

HRID 567813ノート

反応式

HRID 567813 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-4ae1adef5d8d4b6eb5cbd8c118b75bfe
出典データセット
uspto-grants-2001_01
特許番号
US06180627B2

反応ノート

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