Hydrochloric Acid → 5-(3,4-Dichlorophenoxy)-2-hydroxy-3-pyridinecarboxamide

HRID 637801

Reaction equation

HRID 637801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][C:6](=[CH:9]N(C)C)[CH:7]=O.[C:17]([NH2:23])(=[O:22])[CH2:18][C:19]([NH2:21])=[O:20].CC([O-])(C)C.[K+].Cl>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][C:6]1[CH:9]=[C:18]([C:17]([NH2:23])=[O:22])[C:19]([OH:20])=[N:21][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7911MalonamideHCID 23665647Potassium tert-butoxideHCID 545558182-(3,4-Dichlorophenoxy)-3-(dimethylamino)prop-2-enal

Product 1

HCID 1785136925-(3,4-Dichlorophenoxy)-2-hydroxy-3-pyridinecarboxamideYield 43.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

2-(3,4-Dichlorophenoxy)-3-dimethylaminopropenal (13 g), malonamide (5.6 g), and t-BuOK (6.2 g) were mixed in 50 ml of DMSO and heated at 45° C. for 30 minutes. This mixture was then stirred at room temperature for an additional 24 hours after which it was poured into 200 g of an ice-water mixture and acidified with concentrated HCl. A solid formed which was collected by centrifugation, vacuum dried, and recrystallized from 2-propanol to give 6.5 g of the desired 5-(3,4-dichlorophenoxy)-2-hydroxy-3-pyridinecarboxamide, m.p. 246°-249° C.

Workup

  1. customA solid formed which
  2. customwas collected by centrifugation, vacuum
  3. customdried
  4. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-46b63bdf1795404aa60e604ba73f7f82
Source dataset
uspto-grants-1985_12
Patent number
US04558134

Linked notes

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