HCID 18404753, compound → HCID 18404751, compound

HRID 1017694Notes

Reaction equation

HRID 1017694 reaction equation
[C:1]([C:3]1[C:4](=[O:23])[NH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH2:20][CH2:21][CH3:22])[C:12]([O:14]C)=[O:13])=[CH:7][CH:8]=1)#[N:2]>[OH-].[Na+]>[C:1]([C:3]1[C:4](=[O:23])[NH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH2:20][CH2:21][CH3:22])[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 1

HCID 18404753HCID 18404753, compound

Product 1

HCID 18404751HCID 18404751, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 3-(3-cyano-1,2-dihydro-2-oxo-6-pyridinyl)-4-propoxybenzoate (2.0 g) and 1 Normal sodium hydroxide (30 ml) was heated under reflux for 45 minutes and the resultant solution was acidified to give a quantitative yield of 3-(3-cyano-1,2-dihydro-2-oxo-6-pyridinyl)-4-propoxybenzoic acid, m.p. 277-279° C. This acid was heated with thionyl chloride (10 ml) for 90 minutes, the solution was evaporated, and the acid chloride was dissolved in dichloromethane (60 ml). Methylamine was passed slowly through the stirred solution for 45 minutes and both the resultant solid and solution were washed with dilute hydrochloric acid and water. The solid was combined with the residue left after evaporation of the solution to give 1.66 g of solid m.p. 234-236° C. Recrystallization from ethanol gave the title compound, m.p. 235-237° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes

Sources & evidence

ORD record
ord-8fb1d8aa88ea438182649d16358028c2
Source dataset
uspto-grants-2002_11
Patent number
US06479520B1

Reaction notes

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