Hydrochloric Acid → HCID 12394529, compound

HRID 378795Notes

Reaction equation

HRID 378795 reaction equation
[Br:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:13]O>>[Br:1][C:2]1[C:3]([C:9]([O:11][CH3:13])=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21696626HCID 21696626, compound

Product 1

HCID 12394529HCID 12394529, compound

Procedure

To a solution of 3-bromo-4-chloropyridine-2-carboxylic acid (1.75 g, 7.4 mmol) in MeOH was added anhydrous HCl. The resulting mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated to give a solid, which was partitioned between Et2O and saturated NaHCO3. Organic layer was dried over MgSO4, filtered and concentrated to give a brown residue. This material was purified via flash column chromatography to yield 1.35 g of product as a pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a solid, which
  3. customwas partitioned between Et2O and saturated NaHCO3
  4. dry with materialOrganic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown residue
  8. customThis material was purified via flash column chromatography

Sources & evidence

ORD record
ord-c790236f9219433b8aff545c7ad3e99f
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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