Hydrochloric Acid → HCID 70895895, compound

HRID 1519045Notes

Reaction equation

HRID 1519045 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:19][O-].[Na+].Cl>>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[C:11]([Cl:19])=[C:12]([CH3:15])[NH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 63247195-(benzyloxy)-2-methylpyridin-4(1H)-oneHCID 23665760Sodium Hypochlorite

Product 1

HCID 70895895HCID 70895895, compoundYield 86%

Procedure

To a solution of 5-(benzyloxy)-2-methylpyridin-4(1H)-one (9.00 g, 41.8 mmol) in 2M sodium hydroxide (62.5 mL, 125 mmol) under ice-water bath, a solution of 10-14% sodium hypochlorite (62.5 mL) was added slowly during 20 minutes. The reaction mixture was stirred at room temperature for another hour. The reaction mixture was carefully neutralized with 6N HCl to pH about 7 with external cooling to keep the internal temperature below 25° C. The solid was filtered and washed with water (3×), then dried in a vacuum oven for overnight. Thus, 5-(benzyloxy)-3-chloro-2-methylpyridin-4(1H)-one (9.03 g) was obtained as a white solid. Yield=86%; 1H NMR (DMSO-D6, 90 MHz) δ (ppm): 11.74 (br. s, 1H), 7.14-7.68 (m, 6H), 5.02 (s, 2H) and 2.33 (s, 3H).

Workup

  1. temperaturewith external cooling
  2. customthe internal temperature below 25° C
  3. filtrationThe solid was filtered
  4. washwashed with water (3×)
  5. customdried in a vacuum oven for overnight

Sources & evidence

ORD record
ord-9e95d423b749407581d3b15caa11cce9
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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