Hydrochloric Acid → (4-Methoxycarbonylphenyl)-(3-hydroxypyridin-4-yl)-methanol hydrochloride

HRID 2116489Notes

Reaction equation

HRID 2116489 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[O:19]COC)[OH:12])=[CH:7][CH:6]=1)=[O:4].[ClH:23]>CO>[ClH:23].[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[OH:19])[OH:12])=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69220240(4-Methoxycarbonylphenyl)-[3-(methoxymethoxy)pyridin-4-yl]-methanol

Product 1

HCID 23103650(4-Methoxycarbonylphenyl)-(3-hydroxypyridin-4-yl)-methanol hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, a mixture of (4-methoxycarbonylphenyl)-[3-(methoxymethoxy)pyridin-4-yl]-methanol (2.06 g, 6.79 mmol), methanol (35 mL) and concentrated hydrochloric acid (4.4 mL) was heated under reflux for 20 minutes. After cooling to room temperature, the reaction mixture was concentrated. Methanol and ethyl acetate were added to the residue and the resulting precipitate was filtered to give (4-methoxycarbonylphenyl)-(3-hydroxypyridin-4-yl)-methanol hydrochloride (1.87 g, 81%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 minutes
  3. concentrationthe reaction mixture was concentrated
  4. additionMethanol and ethyl acetate were added to the residue
  5. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-7ac00c7dfd4f4115be1636b672730a99
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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