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

HRID 255563노트

반응식

HRID 255563 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-478e253fb3b648fea304f1c3bd2a692b
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04698348

반응 노트

불러오는 중…