Benzyl Alcohol → (7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH:8]=[CH:9][NH:10]2)=[CH:5][C:4]=1C(O)=O.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C>CN(C)C=O>[CH2:17]([O:24][C:47](=[O:32])[NH:44][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[NH:10][CH:9]=[CH:8][C:7]2=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
After dissolving 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (2.58 g) in N,N-dimethylformamide (50 ml), there were added benzyl alcohol (3.29 ml), diphenylphosphoryl azide 2.51 ml) and triethylamine (1.63 ml), and the mixture was heated and stirred at 95° C. for 5 hours. The reaction solution was poured into saturated saline and extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and concentrated. The obtained residue was subjected to NH silica gel column chromatography and eluted with a solvent (ethyl acetate:methanol=5:1) to obtain the title compound (2.03 g) as a solid.
Workup
- temperaturethe mixture was heated
- additionThe reaction solution was poured into saturated saline
- extractionextracted with ethyl acetate
- dry with materialthe organic layer was dried over magnesium sulfate
- concentrationconcentrated
- washeluted with a solvent (ethyl acetate:methanol=5:1)
Sources & evidence
- ORD record
- ord-259c0c9e42c94f7cb36e04b75029879b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372981B2
Reaction notes
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