Ethanol → 7-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

HRID 909337

反応式

HRID 909337 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22].C(O)C>C(#N)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[C:22]([CH2:21][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

参加物

6

反応物 3

HCID 702EthanolHCID 84189Ethoxyacetyl chlorideHCID 690787337-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine

生成物 1

HCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline収率 67.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒2 回

実験手順

7-Bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine (45 g) was dissolved in acetonitrile (1.3 L) and triethylamine (19.4 mL). Ethoxyacetyl chloride (18.0 g) was added dropwise to the solution and the reaction was stirred for 16 hours. The solvent was removed under reduced pressure to afford a tan solid. The solid was added to a solution of ethanol (1 L) and triethylamine (77.5 mL) and heated at reflux for 4 hours. The solvent was removed under reduced pressure. Water was added to the solid residue and the crude product was recovered by filtration. Recrystallization from acetonitrile yielded 36.25 g of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline as a tan crystalline solid.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customto afford a tan solid
  3. temperatureheated
  4. temperatureat reflux for 4 hours
  5. customThe solvent was removed under reduced pressure
  6. additionWater was added to the solid residue
  7. filtrationthe crude product was recovered by filtration
  8. customRecrystallization from acetonitrile

出典と根拠

ORDレコード
ord-134fed903e6046ffa77168d789ca7fdf
出典データセット
uspto-grants-2011_09
特許番号
US08017779B2

関連ノート

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