Hydrochloric Acid → 5,8-Dichloroimidazo-[1,2-a]-quinoline-2-carboxylic acid

HRID 1277967Notes

Reaction equation

HRID 1277967 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]2[CH:13]=[C:14]([C:16]([O:18]CC)=[O:17])[N:15]=[C:4]2[CH:3]=1.[OH-].[Na+].C(COC)OC.Cl>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]2[CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 12763976Ethyl 5,8-dichloroimidazo-[1,2-a]-quinoline-2-carboxylate

Product 1

HCID 127639755,8-Dichloroimidazo-[1,2-a]-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.24 g of ethyl 5,8-dichloroimidazo-[1,2-a]-quinoline-2-carboxylate were hydrolyzed with 3 ml of 2 N sodium hydroxide solution in 120 ml of 50--50 mixture of dimethoxyethane and ethanol. The resultant mixture was neutralized with 3.3 ml of 2 N hydrochloric acid by the method of Example 20 to obtain fine off-white crystals of 5,8-dichloroimidazo-[1,2-a]-quinoline-2-carboxylic acid melting at ≈305° C. (decomp).

Sources & evidence

ORD record
ord-f123739e905c4db1a170cb8e0e6028e8
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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