Triethylamine → 1-Benzyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

HRID 919670Notes

Reaction equation

HRID 919670 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

HCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 728337734-(1-Benzylamino-ethylidene)-pent-2-enedioic acid dimethyl ester

Product 1

HCID 682971751-Benzyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl esterYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperaturewas refluxed for 23 h
  2. temperaturethe mixture was refluxed for 16 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between saturated NH4Cl (100 mL) and CH2Cl2 (100 mL)
  5. addition1M HCl was added until pH was about 1
  6. extractionThe aqueous layer was extracted with additional CH2Cl2
  7. dry with materialthe combined organic layer was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-165cb0fc0535430eab1213fc97794155
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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