Ammonia → 4-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol

HRID 1789441Notes

Reaction equation

HRID 1789441 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:20]>CO>[NH2:20][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 98384584-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 1307144-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.1 g (0.004 mole) of 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline and 30 ml of 15 to 20% ammonia in methanol was heated at 150° to 160° C. for five hours in a bomb reactor. The mixture was filtered and the solid washed sequentially with methanol, ethyl acetate, water, and methanol then dried. Recrystallization from a mixture of ethyl acetate and methanol gave white solid 4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline, m.p. 270°-272° C., Analysis: Calculated for C14H16N4O: % C, 65.6; % H, 6.3; % N, 21.9; Found: % C, 65.6; %H, 6.3; % N, 21.9.

Workup

  1. temperaturewas heated at 150° to 160° C. for five hours in a bomb reactor
  2. filtrationThe mixture was filtered
  3. washthe solid washed sequentially with methanol, ethyl acetate, water, and methanol
  4. customthen dried
  5. customRecrystallization
  6. additionfrom a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-37ae88eabedd477fbfe382c31767cfc2
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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