Ammonia → 2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethanol

HRID 1789429Notes

Reaction equation

HRID 1789429 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:18]>CO>[OH:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:18])[C:11]=2[N:12]=[CH:13]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 139584264-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 113566282-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.0 g (0.016 mole) of 4-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline (from Example 118) and 30 ml of 10% ammonia in methanol was heated in a steel bomb for 12 hours at 150° C. The resulting solid was separated from the cooled mixture by filtration, and was washed sequentially with water and methanol. The air-dried solid was recrystallized from N,N-dimethylformamide to provide white solid 1-(2-hydroxyethyl)-1H-imidazo[4,5-c]-quinolin-4-amine, m.p. 260°-262° C. Analysis: Calculated for C12H12N4O: % C, 63.1; % H, 5.3; % N, 24.5; Found: % C, 63.0; % H, 5.2; % N, 24.3.

Workup

  1. customThe resulting solid was separated from the cooled mixture by filtration
  2. washwas washed sequentially with water and methanol
  3. customThe air-dried solid was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-cb431508c7dd457ab6337acbc87ef42d
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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