Lithium hydroxide, monohydrate → 4,5-Dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792812Notes

Reaction equation

HRID 1792812 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH:10]=1)=[O:8])C>O1CCCC1.O.Cl>[C:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH:10]=1)([OH:8])=[O:6]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22024966Ethyl 4,5-dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 220249714,5-Dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.89 g (45 mmol) of lithium hydroxide monohydrate are added at a temperature in the region of 20° C. to 1.3 g (4.42 mmol) of 3-ethoxycarbonyl-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 42 hours, the reaction mixture is concentrated virtually to dryness under reduced pressure (2.7 kPa) to give a residue that is taken up in 41 mL of 1N hydrochloric acid. After filtering off and drying the solid residue at ambient pressure at a temperature in the region of 50° C., 1.1 g of 3-carboxy-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole are obtained in the form of a whitish solid melting at approximately 238° C.

Workup

  1. temperatureat reflux for 42 hours
  2. concentrationthe reaction mixture is concentrated virtually to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue that
  4. filtrationAfter filtering off
  5. dry with materialdrying the solid residue at ambient pressure at a temperature in the region of 50° C., 1.1 g of 3-carboxy-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole

Sources & evidence

ORD record
ord-2a5c448614724de781c0c90100dd80fc
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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