Hydrochloric Acid → HCID 54438576, compound
Reaction equation
[CH3:1][Li].[CH3:3][C:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][C:5]=1[C:17]([OH:19])=O.Cl>C(OCC)C>[C:17]([C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:15][C:16]=2[C:4]=1[CH3:3])(=[O:19])[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
15 ml of a 1.5M solution of methyllithium (22 mmol) in diethyl ether was added to 30 ml of a solution of 1.25 g of 1-methylcarbazol-2-ylcarboxylic acid (5.5 mmol--as obtained in Example 26) in diethyl ether, at a temperature of -78° C. The reaction mixture was then warmed to room temperature and stirred for 1 hour. After this time, the mixture was poured into a 0.5N aqueous solution of hydrogenchloride. The aqueous layer was extracted with ethyl acetate and the resulting organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate, and the solvent was then removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 25% v/v solution of ethyl acetate in hexane) to yield 1.08 g (88%) of the title compound as an amorphous solid.
Workup
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe resulting organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate
- dry with materiala saturated aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate
- customthe solvent was then removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-7d4fe6e724994040b2af33736d967528
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877199
Reaction notes
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