Lithium hydroxide, monohydrate → 1-(Isoquinolin-1-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792794Notes

Reaction equation

HRID 1792794 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:12]=[CH:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=1)=[O:7]>O1CCCC1.O>[C:6]([C:8]1[CH:12]=[CH:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22024958Methyl 1-(isoquinolin-1-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 220249831-(Isoquinolin-1-yl)-1H-pyrrole-3-carboxylic acidYield 107.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.237 g (5.65 mmol) of lithium hydroxide monohydrate is added at 20° C. to 0.57 g (2.26 mmol) of 3-methoxycarbonyl-1-(isoquinol-1-yl)-1H-pyrrole dissolved in 15 mL of tetrahydrofuran and 15 mL of water. After stirring at reflux for 2 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 5 mL of water and then triturated with 5.65 mL of N hydrochloric acid for 1 hour. The aqueous phase is filtered and the solid residue is washed with twice 5 mL of water and then air-dried to give 0.58 g of 3-carboxy-1-(isoquinol-1-yl)-1H-pyrrole in the form of a white solid. Mass spectrum (EI): m/e 238 (M+.), m/e 193.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. customtriturated with 5.65 mL of N hydrochloric acid for 1 hour
  5. filtrationThe aqueous phase is filtered
  6. washthe solid residue is washed with twice 5 mL of water
  7. customair-dried

Sources & evidence

ORD record
ord-96c3dc202bcb4abf93b24b0126811e26
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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