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

HRID 1006664노트

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HRID 1006664 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
82.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac9c19372a234a0fb78b153b298efe3b
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790960B2

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