Ammonia → 2-(Hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]pyridin-4(1H)-one

HRID 639033Notes

Reaction equation

HRID 639033 reaction equation
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[NH3:20]>C(O)C>[OH:1][CH2:2][C:3]1[NH:20][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

Product 1

HCID 151595322-(Hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]pyridin-4(1H)-oneYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(hydroxymethyl)-5-({[4-(methoxy)phenyl]methyl}oxy)-4(1H)-pyrone (40 g, 153 mmol) in ethanol (105 mL) was added concentrated aqueous ammonia (295 mL) and refluxed for 18 hours. The mixture was cooled, then refrigerated for 3 hours, and cooled in an ice-bath for 45 minutes. The solid was filtered off, washed with cold ethanol, followed by cold petroleum ether and dried in vacuo to afford the product as brown solid (26.21 g, 66%).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe mixture was cooled
  3. temperaturecooled in an ice-bath for 45 minutes
  4. filtrationThe solid was filtered off
  5. washwashed with cold ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cb3b5c28e23b40f78cddb89d28b92460
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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