Ammonia → 4-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline

HRID 255520Notes

Reaction equation

HRID 255520 reaction equation
C([O:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([Cl:25])[C:15]=2[N:14]=[CH:13]1)(=O)C1C=CC=CC=1.N>CO>[Cl:25][C:16]1[C:15]2[N:14]=[CH:13][N:12]([CH2:11][CH2:10][OH:9])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 139584251-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 25.3 g (0.072 mole) of 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline (from Example 120) and 500 ml of 10% ammonia in methanol was stirred at about 20° C. for three days, and was filtered and then evaporated to low volume. The slurry was mixed with diethyl ether, and the solid was separated by filtration, washed with ether and recrystallized from methanol to provide white crystals of 4-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline, m.p. 185°-187° C. Analysis: Calculated for C12H10ClN3O: %C, 58.2; %H, 4.1; %N, 17.0; Found: %C, 58.0; %H, 4.0; %N, 17.3.

Workup

  1. filtrationwas filtered
  2. customevaporated to low volume
  3. additionThe slurry was mixed with diethyl ether
  4. customthe solid was separated by filtration
  5. washwashed with ether
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-aeaf32041c0742b8bcfcd7365c2afd0e
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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