Hydrochloric Acid → HCID 21948386, compound

HRID 1276289Notes

Reaction equation

HRID 1276289 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.Cl.[CH3:20]O>>[NH2:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([O:16][CH3:20])=[O:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70295713HCID 70295713, compound

Product 1

HCID 21948386HCID 21948386, compoundYield 70%

Procedure

A stirred suspension of 4-(6-amino-2-methylpyridin-3-yl)benzoic acid hydrochloride (D6, 1.9 g, 8.3 mmole) in methanol (120 ml) was treated with conc. HCl acid (1 ml) and heated under reflux for 2 h. The solution was concentrated in vacuo, the residue treated with excess 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a pale yellow solid (1.4 g, 70%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. concentrationThe solution was concentrated in vacuo
  4. additionthe residue treated with excess 10% Na2CO3 solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-449625e405d44150b6051e2c4e4a8e2f
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Reaction notes

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