Dimethylformamide → HCID 68830320, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:16]#[N:17])=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.[C:25]([O:28][CH2:29][CH2:30]Br)(=[O:27])[CH3:26].CN(C)C=O>O>[C:25]([O:28][CH2:29][CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:16]#[N:17])=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:27])[CH3:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 6-hydroxy-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (5.0 g, 15.8 mmol), 2-bromoethyl acetate (3.2 g, 19 mmol) and N,N-dimethylformamide (20 ml) was stirred at 50° C. for 15 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous-magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether and filtered to give 2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}ethyl acetate (5.0 g, yield 79%) as crystals.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
- dry with materialdried over anhydrous-magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was crystallized from diethyl ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-8edad0973dbe49d1a23d563d99418237
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547710B2
Reaction notes
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