Acetic Acid → Ethyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate
Reaction equation
C([C:3]1[C:11]([N+:12]([O-])=O)=[C:10]([CH:15]=[CH:16][C:17]([O:19]C)=O)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])C.[C:21](O)(=O)[CH3:22]>[Pd]>[O:19]=[C:17]1[CH2:16][CH2:15][C:10]2[C:11](=[CH:3][C:4]([C:5]([O:7][CH2:21][CH3:22])=[O:6])=[CH:8][CH:9]=2)[NH:12]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
The solution of 2.80 g of ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid in 20 ml of glacial acetic acid is hydrogenated in the presence of 0.288 g of 10% Pd/C at room temperature over 16 hours. The reaction mixture is stirred at 70° C. over 1 hour and subsequently concentrated by evaporation to dryness. The residue is admixed with 250 ml of 1M sodium hydrogencarbonate and extracted with ethyl acetate (2×250 ml). The organic phases are washed with water (250 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of crystallization (ethyl acetate-hexane). Rf=024 (1:1 EtOAc-heptane).
Workup
- concentrationsubsequently concentrated by evaporation to dryness
- extractionextracted with ethyl acetate (2×250 ml)
- washThe organic phases are washed with water (250 ml)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-eb0d8509c73c4146a37fd2c5eb64f3ea
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790715B2
Reaction notes
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