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

HRID 627112Notes

Reaction equation

HRID 627112 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]>>[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

3

Reactant 2

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

Product 1

HCID 151595322-(Hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]pyridin-4(1H)-one

Conditions

Temperature
90 °C

Procedure

2-(hydroxymethyl)-5-(4-methoxybenzyloxy)-4H-pyran-4-one (Intermediate 63, 6.44 g, 24.56 mmol) and ammonia (7N in MeOH) (59.6 ml, 417.45 mmol) were combined in a pressure reactor vessel and heated at 90° C. for 5 hours. The reaction mixture was cooled overnight then concentrated. The solid was suspended in water then collected by filtration. The title compound was obtained as a brown solid (3.48 g, 54%).

Workup

  1. temperatureThe reaction mixture was cooled overnight
  2. concentrationthen concentrated
  3. filtrationthen collected by filtration

Sources & evidence

ORD record
ord-07ca78d89c3e496780f8984d4c10b403
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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