Ammonia → 1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride hydrate

HRID 1789420Notes

Reaction equation

HRID 1789420 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:8])C1C=CC=CC=1.[NH3:26]>CO.Cl>[OH2:8].[ClH:25].[OH: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]([NH2:26])[C:15]=2[N:14]=[CH:13]1

Participants

5

Reactant 2

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

Product 1

HCID 139828911-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride hydrate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 1.3 g (0.0037 mole) of 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline (from Example 117) in 60 ml of methanol was saturated with about 10g of ammonia gas. The mixture was heated at 150° C. in a steel bomb for ten hours. The mixture was evaporated, and the residue was slurried in diethyl ether and filtered. The solid obtained was slurried in methanolic hydrochloric acid to provide off-white solid 1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride hydrate, m.p. >250° C. Analysis: Calculated for C12H12N4O·HCl·1.25H2O: C, 50.2; % H, 5.4; % N, 19.5; Found: % C, 50.2; % H, 5.2; % N, 19.1.

Workup

  1. customThe mixture was evaporated
  2. filtrationfiltered
  3. customThe solid obtained

Sources & evidence

ORD record
ord-d55cf3cb02ba41bab50cae8993ff9059
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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