Lithium hydroxide, monohydrate → 1-(Isoquinolin-1-yl)-4-methyl-1H-pyrrole-3-carboxylic acid
Reaction equation
O.[OH-].[Li+].[C:4]1([N:14]2[CH:18]=[C:17]([CH3:19])[C:16]([C:20]([O:22]C)=[O:21])=[CH:15]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1>O1CCCC1.O>[C:20]([C:16]1[C:17]([CH3:19])=[CH:18][N:14]([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[CH:6][N:5]=2)[CH:15]=1)([OH:22])=[O:21]Participants
5
Procedure
0.63 g (15 mmol) of lithium hydroxide monohydrate is added at a temperature in the region of 20° C. to 1.35 g (5 mmol) of 1-(isoquinol-1-yl)-3-methoxycarbonyl-4-methyl-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 25 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 20 mL of water and then triturated with 15 mL of 1N hydrochloric acid. After filtering off and drying the solid residue at ambient pressure at a temperature in the region of 50° C., 1.1 g of 3-carboxy-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole are obtained in the form of a whitish solid melting at 245° C.
Workup
- temperatureat reflux for 25 hours
- concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
- customto give a residue which
- customtriturated with 15 mL of 1N hydrochloric acid
- filtrationAfter filtering off
- dry with materialdrying the solid residue at ambient pressure at a temperature in the region of 50° C., 1.1 g of 3-carboxy-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole
Sources & evidence
- ORD record
- ord-4171eb3662dd4db3925a61d44be6d640
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07078414B2
Reaction notes
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