Water → 1-(Quinolin-5-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792798Notes

Reaction equation

HRID 1792798 reaction equation
O.[OH-].[Li+].O.C[O:6][C:7]([C:9]1[CH:13]=[CH:12][N:11]([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:10]=1)=[O:8]>O1CCCC1>[C:7]([C:9]1[CH:13]=[CH:12][N:11]([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:10]=1)([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22024936Methyl 1-(quinolin-5-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 220249671-(Quinolin-5-yl)-1H-pyrrole-3-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.36 g (8.58 mmol) of lithium hydroxide monohydrate and 20 mL of water are added to a solution at a temperature in the region of 22° C. of 0.5 g (1.98 mmol) of 3-methoxycarbonyl-1-(quinol-5-yl)-1H-pyrrole in 20 mL of tetrahydrofuran. After stirring at the reflux point of the solvent for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is taken up in water. The resulting solution is adjusted to pH 7 using N hydrochloric acid and then it is extracted with ethyl acetate. The organic phase is washed with a saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). 0.42 g of 3-carboxy-1-(quinol-5-yl)-1H-pyrrole is thus obtained in the form of a white solid. IR spectrum (KBr): 3423, 3105, 1665, 1536, 1275, 1188, 1107, 965 and 796 cm−1.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. extractionit is extracted with ethyl acetate
  3. washThe organic phase is washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-07442da8730b42eca62689c2a93e2166
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

Loading…