2-Naphthalenecarboxaldehyde → methyl 6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate

HRID 734657Notes

Reaction equation

HRID 734657 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[CH3:13][C:14]1(C)[O:19]C(=O)CC(=O)O1.[C:23]([O:29][CH3:30])(=[O:28])[CH2:24][C:25]([CH3:27])=O.C([O-])(=O)C.[NH4+:35]>C(O)(=O)C.O>[CH3:27][C:25]1[NH:35][C:14](=[O:19])[CH2:13][CH:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:24]=1[C:23]([O:29][CH3:30])=[O:28]

Participants

7

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 7757Methyl acetoacetateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium Acetate

Product 1

HCID 3863296methyl 6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylateYield 36.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2-Naphthaldehyde (30.0 g, 192 mmol, 1.00 equiv), 2,2-dimethyl-1,3-dioxane-4,6-dione (27.6 g, 192 mmol, 1.00 equiv), methyl acetoacetate (20.7 mL, 192 mmol, 1.00 equiv), and ammonium acetate (15.6 g, 202 mmol, 1.05 equiv) were dissolved in acetic acid (0.20 L) and heated to reflux for 4 hours, then cooled to room temperature. Addition of water (1 L) to the cooled reaction mixture induced formation of a white precipitate. The solid was collected by filtration and triturated with diethyl ether to provide the 20.5 g (36%) of the product as an off-white solid. MS (ES+) m/e 296 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customto the cooled reaction mixture
  4. filtrationThe solid was collected by filtration
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-4043351671a246aa8bee72405c68eb0a
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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