Hydrochloric Acid → 3-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-(hydroxymethyl)quinoline hydrochloride

HRID 1647445

Reaction equation

HRID 1647445 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:25][O:26]C(=O)C1C=CC(OC)=CC=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].[ClH:39]>CO.O>[ClH:39].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:25][OH:26])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 199096773-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-(4-methoxybenzoyloxymethyl)quinoline

Product 1

HCID 199230143-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-(hydroxymethyl)quinoline hydrochlorideYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-8-(4-methoxybenzoyloxymethyl)quinoline (2.34 g, 4.8 mmol) and sodium hydroxide (0.38 g, 9.6 mmol) in methanol (50 ml) was heated at reflux for 30 minutes, then diluted with water and neutralised with dilute hydrochloric acid. The solid was filtered off and washed with water, then converted to the hydrochloride. Recrystallisation from aqueous ethanol gave 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-8-(hydroxymethyl)quinoline hydrochloride (1.16 g, 62%), m.p. 167°-171°.

Workup

  1. temperatureat reflux for 30 minutes
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customRecrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-3166ce2ab0fc4aa18be4c3feb5149d35
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Linked notes

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