Dimethylformamide → 4-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 255563ノート

反応式

HRID 255563 の反応式
C([O:4][C:5]([CH3:22])([CH3:21])[CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:12]([O-])=[CH:11][C:10]=2[N:9]=[CH:8]1)(=O)C.CN(C)C=O.P(Cl)(Cl)([Cl:30])=O>ClCCl>[Cl:30][C:11]1[C:10]2[N:9]=[CH:8][N:7]([CH2:6][C:5]([OH:4])([CH3:22])[CH3:21])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 201835851-(2-acetoxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-5-oxide

生成物 1

HCID 98384584-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 1.5 g of crude 1-(2-acetoxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-5-oxide from Part C in 10 ml of dichloromethane and 2 ml of N,N-dimethylformamide was added 0.843 g (0.0055 mole) of phosphorus oxychloride. After stirring for one hour, the mixture was evaporated to dryness. Hydrochloric acid was added to the residue, then the mixture was basified with ammonium hydroxide. The product was separated by filtration, washed with water and dried. Recrystallization from ethanol of a portion of the product provided 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline, m.p. 196°-199° C. Analysis: Calculated for C14H14ClN3O: %C, 61.0; %H, 5.2; %N, 15.2; Found: %C, 60.9; %H, 5.3; %N, 15.1.

後処理

  1. customthe mixture was evaporated to dryness
  2. additionHydrochloric acid was added to the residue
  3. customThe product was separated by filtration
  4. washwashed with water
  5. customdried
  6. customRecrystallization from ethanol of a portion of the product

出典と根拠

ORDレコード
ord-478e253fb3b648fea304f1c3bd2a692b
出典データセット
uspto-grants-1987_10
特許番号
US04698348

反応ノート

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