Hydrochloric Acid → 5-((4-Methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

HRID 525852Notes

Reaction equation

HRID 525852 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])O[CH:14]=2)=[CH:5][CH:4]=1.[CH3:21][NH2:22].Cl>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[N:22]([CH3:21])[CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 150777735-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 708124915-((4-Methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acidYield 79%

Procedure

A mixture of 5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carboxylic acid (1.4627 g, 5.30 mmol) and methanamine (11.0 ml, 22.00 mmol) was stirred at room temperature for 20 h, The reaction was concentrated under reduced pressure, and the residue was dissolved in 15 mL of de-ionized water. The aqueous solution was cooled in an ice bath and treated dropwise with 2N hydrochloric acid (3.0 ml, 6.00 mmol). The resulting yellow solid was filtered, washed with water and acetone, and dried to give 5-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (1.21 g, 4.18 mmol, 79% yield). LCMS: (M+H)+: 290.1.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 15 mL of de-ionized water
  3. temperatureThe aqueous solution was cooled in an ice bath
  4. filtrationThe resulting yellow solid was filtered
  5. washwashed with water and acetone
  6. customdried

Sources & evidence

ORD record
ord-648f63be3bb74487b1afb6845afa3114
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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