Nitric Acid → 2,3-Dimethyl-8-(2,6-dimethylbenzylamino)-7-nitroimidazo[1,2-a]pyridine

HRID 1369560ノート

反応式

HRID 1369560 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][CH:7]=[CH:6][N:5]2[C:20]=1[CH3:21].[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[CH3:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:20]([CH3:21])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[CH:7][C:8]=1[N+:22]([O-:24])=[O:23]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 226726292,3-Dimethyl-8-(2,6-dimethylbenzylamino)imidazo[1,2-a]pyridine

生成物 1

HCID 226726012,3-Dimethyl-8-(2,6-dimethylbenzylamino)-7-nitroimidazo[1,2-a]pyridine収率 17.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
82.5 °C

実験手順

2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine (2.0 g, 7.16 mmol) was dissolved in acetic acid (30 ml) and nitric acid (0.53 g, 7.57 mmol) was added. The mixture was heated to 80-85° C. and stirred for 3 h at this temperature. After evaporation of the major part of the acetic acid, the residue was partitioned between methylene chloride and water. The organic layer was washed with a solution of sodium carbonate and the solvent was removed under reduced pressure. The residue was dissolved in methylene chloride (100 ml) and filtered through silica gel (10 g) whereupon the methylene chloride was removed under reduced pressure. Chromatography with methylene chloride (100%) gave 0.4 g (17%) of the title compound.

後処理

  1. customAfter evaporation of the major part of the acetic acid
  2. customthe residue was partitioned between methylene chloride and water
  3. washThe organic layer was washed with a solution of sodium carbonate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride (100 ml)
  6. filtrationfiltered through silica gel (10 g) whereupon the methylene chloride
  7. customwas removed under reduced pressure

出典と根拠

ORDレコード
ord-be32d2f5a7e84ed1bcc61181cb3526d5
出典データセット
uspto-grants-2003_06
特許番号
US06579884B1

反応ノート

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