Hydrochloric Acid → 2-(5-Bromo-2-hydroxybenzoyl)-3-hydroxypyridine

HRID 862061Notes

Reaction equation

HRID 862061 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20]COC)=[C:6]([CH:19]=1)[C:7]([C:9]1[C:14]([O:15]COC)=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8].Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:19]=1)[C:7]([C:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 197015972-(5-Bromo-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine

Product 1

HCID 108276052-(5-Bromo-2-hydroxybenzoyl)-3-hydroxypyridineYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(5-bromo-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine (1.89 g), hydrochloric acid (10 ml) and methanol (80 ml) was stirred for 70 hours at room temperature. The reaction mixture was concentrated, which was partitioned with ethyl acetate-water. The organic layer was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 2-(5-bromo-2-hydroxybenzoyl)-3-hydroxypyridine (1.34 g) (Compound A-1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwhich was partitioned with ethyl acetate-water
  3. washThe organic layer was washed with a saturated aqueous saline solution
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-600b6b3aa09c46bcac0d864d27408177
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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