Triethylamine → 1-Benzyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester
Reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.C[O-].[Na+]>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[CH:4][C:3](=[O:2])[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[CH3:12])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-(1-benzylamino-ethylidene)-pent-2-enedioic acid dimethyl ester (3 g, 10.4 mmol), triethylamine (1.5 mL, Et3N) and MeOH (200 mL) was refluxed for 23 h. NaOMe solution (0.12 mL, 0.52 mmol, 25 wt % in MeOH) was added, and the mixture was refluxed for 16 h. The mixture was cooled to r.t. and concentrated in vacuo. The residue was partitioned between saturated NH4Cl (100 mL) and CH2Cl2 (100 mL). 1M HCl was added until pH was about 1. The aqueous layer was extracted with additional CH2Cl2, and the combined organic layer was dried over MgSO4 and concentrated to give 2.64 g of the title compound as a white solid. MS: (+) m/z 258.13 (M+1).
Workup
- temperaturewas refluxed for 23 h
- temperaturethe mixture was refluxed for 16 h
- concentrationconcentrated in vacuo
- customThe residue was partitioned between saturated NH4Cl (100 mL) and CH2Cl2 (100 mL)
- addition1M HCl was added until pH was about 1
- extractionThe aqueous layer was extracted with additional CH2Cl2
- dry with materialthe combined organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6bc490f280ae4cc7a1133417485dd6bb
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921389B2
Reaction notes
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