Hydrochloric Acid → 2-Methyl-1-(quinolin-2-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792791Notes

Reaction equation

HRID 1792791 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[CH:13]=[CH:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[C:10]=1[CH3:24])=[O:8])C.Cl>O1CCCC1.O>[C:7]([C:9]1[CH:13]=[CH:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[C:10]=1[CH3:24])([OH:8])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22024946Ethyl 2-methyl-1-(quinolin-2-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 220249772-Methyl-1-(quinolin-2-yl)-1H-pyrrole-3-carboxylic acidYield 111.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3.9 g (93 mmol) of lithium hydroxide monohydrate, portionwise every 24 hours, are added at 20° C. to 1.9 g (6.78 mmol) of 3-ethoxycarbonyl-2-methyl-1-(quinol-2-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 72 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue that is taken up in 75 mL of water. The pH of the aqueous phase is adjusted to 2 by addition of concentrated hydrochloric acid. After stirring for 1 hour, the aqueous phase is filtered and the solid residue is dried under reduced pressure (2.7 kPa) at 40° C. to give 1.9 g of 3-carboxy-2-methyl-1-(quinol-2-yl)-1H-pyrrole in the form of a beige-coloured solid.

Workup

  1. temperatureat reflux for 72 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue that
  4. stirringAfter stirring for 1 hour
  5. filtrationthe aqueous phase is filtered
  6. customthe solid residue is dried under reduced pressure (2.7 kPa) at 40° C.

Sources & evidence

ORD record
ord-2554c89ae0a34a9ea0efbd031f33274b
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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