HCID 66869298, compound → HCID 88984999, compound

HRID 1519049Notes

Reaction equation

HRID 1519049 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[C:13]([Cl:16])=[CH:12][N:11]([CH3:17])[CH:10]=1)C1C=CC=CC=1>Cl.C(O)C>[Cl:16][C:13]1[C:14](=[O:15])[C:9]([OH:8])=[CH:10][N:11]([CH3:17])[CH:12]=1

Participants

4

Reactant 1

HCID 66869298HCID 66869298, compound

Product 1

HCID 88984999HCID 88984999, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-(Benzyloxy)-5-chloro-1-methylpyridin-4(1H)-one (2.70 g, 10.8 mmol) was mixed in 6N HCl (15 mL) and ethanol (10 mL). After being refluxed for 2 hours, the reaction mixture was concentrated by rotary evaporator. The residue was mixed with water (5 mL) and basified to pH 8-9 with concentrated ammonia. An off-white precipitate came out, and the mixture was again concentrated in vacuo to remove volatiles. The off-white solid was collected by suction filtration and dried to give 3-chloro-5-hydroxy-1-methylpyridin-4(1H)-one (1.32 g). Yield=76.6%; 1H NMR (DMSO-D6, 90 MHz) δ(ppm): 7.98 (s, 1H), 7.47 (s, 1H) and 3.67 (s, 3H).

Workup

  1. temperatureAfter being refluxed for 2 hours
  2. concentrationthe reaction mixture was concentrated by rotary evaporator
  3. additionThe residue was mixed with water (5 mL)
  4. concentrationthe mixture was again concentrated in vacuo
  5. customto remove volatiles
  6. filtrationThe off-white solid was collected by suction filtration
  7. customdried

Sources & evidence

ORD record
ord-546899a964304dbfa17c3f0c4e5bebd0
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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