Hydrochloric Acid → HCID 67366489, compound

HRID 1910933Notes

Reaction equation

HRID 1910933 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][N:10]2[C:15](=[O:16])[CH:14]=[CH:13][CH:12]=[C:11]2[C:17]([O:19]C)=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][N:10]2[C:15](=[O:16])[CH:14]=[CH:13][CH:12]=[C:11]2[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67367655HCID 67367655, compound

Product 1

HCID 67366489HCID 67366489, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of methyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-6-oxo-1,6-dihydropyridine-2-carboxylate (130 mg, 0.43 mmol) in MeOH (5 mL) and water (2.5 mL) was added a aqueous solution of NaOH (1 M) (0.8 mL, 0.8 mmol). The resulting dark orange solution was stirred at room temperature until completion (45 minutes, monitored by LCMS). The mixture was then acidified with an aqueous solution of HCl (1 M) and the resulting suspension was concentrated in vacuo to remove the MeOH. The precipitate formed was collected by filtration and washed with water to yield the acid derivative 1-[2-(4-chlorophenyl)-2-oxoethyl]-6-oxo-1,6-dihydropyridine-2-carboxylic acid as a yellow solid (100 mg, 80%). 1H NMR (400 MHz, d6-DMSO): 5.84 (s, 2H), 6.73 (dd, 1H, J 9.2, 1.2 Hz), 7.01 (dd, 1H, J 6.8, 1.0 Hz), 7.57 (dd, 1H, J 9.2, 6.9 Hz), 7.66 (d, 2H, J 8.6 Hz), 8.07 (d, 2H, J 8.5 Hz).

Workup

  1. concentrationthe resulting suspension was concentrated in vacuo
  2. customto remove the MeOH
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-024fd8a53f6f486281507cf1a9e047ec
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

Loading…