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

HRID 1792805Notes

Reaction equation

HRID 1792805 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:9]=1)=[O:7]>O1CCCC1.O>[C:6]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22024954Methyl 4-methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 220249694-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.63 g (15 mmol) of lithium hydroxide monohydrate is added at a temperature in the region of 20° C. to 1.21 g (4.54 mmol) of 3-methoxycarbonyl-4-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 22 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 20 mL of water and then triturated with 15 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., 1.05 g of 3-carboxy-4-methyl-1-(quinol-4-yl)-1H-pyrrole are obtained in the form of a whitish solid. Mass spectrum (EI): EI: m/e 252 (M+.) m/e 207.

Workup

  1. temperatureat reflux for 22 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. customtriturated with 15 mL of 1N hydrochloric acid
  5. filtrationAfter filtering off
  6. dry with materialdrying the solid residue at ambient pressure at a temperature in the region of 50° C., 1.05 g of 3-carboxy-4-methyl-1-(quinol-4-yl)-1H-pyrrole
  7. customare obtained in the form of a whitish solid

Sources & evidence

ORD record
ord-f2bee4fff69a42e4b9e7a6127aaa4781
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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