Water → HCID 22024991, compound

HRID 1792821Notes

Reaction equation

HRID 1792821 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[CH:9]=1)=[O:7].O>O1CCCC1>[C:6]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22024955Methyl 4-methyl-1-(quinolin-5-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 22024991HCID 22024991, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.504 g (12.2 mmol) of lithium hydroxide monohydrate is added to 0.8 g (3.04 mmol) of 3-methoxycarbonyl-4-methyl-1-(quinolin-5-yl)-1H-pyrrole dissolved in 25 mL of tetrahydrofuran and 25 mL of water at a temperature in the region of 20° C. After stirring for 30 hours at the reflux temperature of the solvent, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 20 mL of water and then neutralized with 1 N hydrochloric acid. The mixture is filtered, and the solid residue obtained is dried, giving 0.5 g of 3-carboxy-4-methyl-1-(quinolin-5-yl)-1H-pyrrole in the form of a cream-colored solid, melting above 260° C., which is used directly in the following step.

Workup

  1. customin the region of 20° C
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. filtrationThe mixture is filtered
  4. customthe solid residue obtained
  5. customis dried

Sources & evidence

ORD record
ord-a2213ef54f2049318553c7dac6821260
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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