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

HRID 255563Notes

Reaction equation

HRID 255563 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-478e253fb3b648fea304f1c3bd2a692b
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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