Hydrochloric Acid → HCID 66869089, compound

HRID 1519047Notes

Reaction equation

HRID 1519047 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:19])[C:11]([Cl:18])=[C:12]([CH2:16][OH:17])[N:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[K+].Cl[O-:23].[Na+].Cl>CC(C)=O.C(=O)(O)[O-].[Na+].O.CC1(C)N([O])C(C)(C)CCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[C:11]([Cl:18])=[C:12]([C:16]([OH:23])=[O:17])[N:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 253877Potassium BromideHCID 23665760Sodium HypochloriteHCID 70805221HCID 70805221, compound

Product 1

HCID 66869089HCID 66869089, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 2724126TempoCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 5-(benzyloxy)-3-chloro-2-(hydroxymethyl)-1-methylpyridin-4(1H)-one (4.90 g, 17.5 mmol), TEMPO (120 mg, 0.77 mmol) and potassium bromide (120 mg, 1.00 mmol) in acetone (50 mL) and saturated sodium bicarbonate (40 mL) below 7° C. was added dropwise a 10-14% sodium hypochlorite (50 mL) solution during 30 minutes. After being stirred for 2 hours, the reaction mixture was diluted with water and adjusted to pH about 1.5 with 6N HCl. The solid was filtered and washed with water to give 5-(benzyloxy)-3-chloro-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (2.89 g) as a white solid. Yield=56%; 1H NMR (DMSO-D6, 90 MHz) δ (ppm): 7.79 (s, 1H), 7.16-7.62 (m, 5H), 5.03 (s, 2H) and 3.67 (s, 3H); MS m/z 294 [M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-0cf973853fa84873bd364eaee3b2f4c7
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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