Hydrochloric Acid → 5-(4-chloro-benzyloxy)-2-hydroxymethyl-1H-pyridin-4-one

HRID 1964953Notes

Reaction equation

HRID 1964953 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9](=[O:16])[CH:10]=[C:11]([CH2:14][OH:15])O[CH:13]=2)=[CH:4][CH:3]=1.Cl.[OH-].[NH4+:21]>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9](=[O:16])[CH:10]=[C:11]([CH2:14][OH:15])[NH:21][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 580868345-(4-Chloro-benzyloxy)-2-hydroxymethyl-pyran-4-one

Product 1

HCID 580875645-(4-chloro-benzyloxy)-2-hydroxymethyl-1H-pyridin-4-one

Conditions

Temperature
90 °C

Procedure

5-(4-Chloro-benzyloxy)-2-hydroxymethyl-pyran-4-one (638, 8.00 g, 3.00 mmol) was suspended in ammonium hydroxide (200 mL) in an 80 mL sealed tube. The reaction was heated at 90° C. overnight. Upon cooling, the reaction was lowered to pH 10 with 6N HCl to provide a beige solid that was collected by filtration (639, 7.8 g, 98%).

Workup

  1. customsealed tube
  2. temperatureUpon cooling
  3. customto provide a beige solid
  4. filtrationthat was collected by filtration (639, 7.8 g, 98%)

Sources & evidence

ORD record
ord-1dcf0b3da91f4a0c88917d2c57a5c3e5
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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