Water → 1-(Isoquinolin-4-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792802Notes

Reaction equation

HRID 1792802 reaction equation
O.[OH-].[Li+].O.C[O:6][C:7]([C:9]1[CH:13]=[CH:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[N:16][CH:15]=2)[CH:10]=1)=[O:8].[K+].[Br-]>O1CCCC1>[C:7]([C:9]1[CH:13]=[CH:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[N:16][CH:15]=2)[CH:10]=1)([OH:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 253877Potassium BromideHCID 22024992Methyl 1-(isoquinolin-4-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 220249401-(Isoquinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.63 g (15.02 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 0.95 g (376 mmol) of 3-methoxycarbonyl-1-(isoquinol-4-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 dissolved in water. The solution is extracted with ethyl acetate and the organic phase is discarded. The aqueous phase is adjusted to pH 6 with N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed successively with water and with saturated aqueous sodium chloride solution and then it is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa), resulting in 0.75 g of 3-carboxy-1-(isoquinol-4-yl)-1H-pyrrole in the form of a beige-coloured solid. IR spectrum (KBr): 3153, 2518, 1855, 1690, 1495, 1276, 1188, 933, 808, 783, 757, 712 and 675 cm−1.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. dissolutionthe residue is dissolved in water
  3. extractionThe solution is extracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed successively with water and with saturated aqueous sodium chloride solution
  6. dry with materialit is dried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customresulting in 0.75 g of 3-carboxy-1-(isoquinol-4-yl)-1H-pyrrole in the form of a beige-coloured solid

Sources & evidence

ORD record
ord-a71ed9b08627498493d90473bab0af9f
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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