Lithium hydroxide, monohydrate → 4-Cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid
Reaction equation
O.[OH-].[Li+].[CH:4]1([C:7]2[C:8]([C:22]([O:24]C)=[O:23])=[CH:9][N:10]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=[CH:14][CH:13]=3)[CH:11]=2)[CH2:6][CH2:5]1>O1CCCC1.O>[C:22]([C:8]1[C:7]([CH:4]2[CH2:6][CH2:5]2)=[CH:11][N:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH:9]=1)([OH:24])=[O:23]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
0.63 g (15 mmol) of lithium hydroxide monohydrate is added, at a temperature in the region of 20° C., to 1.3 g (4.4 mmol) of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring for 26 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 triturated with 15 mL of 1 N hydrochloric acid. After the solid residue has been filtered off and dried at a temperature in the region of 50° C. at atmospheric pressure, 1.05 g of 3-carboxy-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole are obtained in the form of a cream-colored solid melting at 195° C.
Workup
- concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
- customtriturated with 15 mL of 1 N hydrochloric acid
- filtrationAfter the solid residue has been filtered off
- dry with materialdried at a temperature in the region of 50° C. at atmospheric pressure, 1.05 g of 3-carboxy-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole
Sources & evidence
- ORD record
- ord-85bef526f5de461aa02d64133e4662c8
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07078414B2
Reaction notes
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