Acetone → 2-(3-Bromobenzoyl)-3-hydroxypyridine

HRID 442724Notes

Reaction equation

HRID 442724 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:12]([O:13]COC)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].S(=O)(=O)(O)O.CC(C)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 539766302-(3-Bromobenzoyl)-3-methoxymethoxypyridine

Product 1

HCID 110331762-(3-Bromobenzoyl)-3-hydroxypyridineYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-bromobenzoyl)-3-methoxymethoxy pyridine (5.55 g), 3.6N-sulfuric acid (11 mL) and acetone (30 mL) was subjected to reflux for 3 hours. The reaction mixture was poured into water, neutralized with an aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromobenzoyl)-3-hydroxypyridine (4.46 g) (compound C-1). Physical properties and spectrum date of the product are shown in Table 5 and Table 6. In substantially the same manner as above, compounds C-2 to C-4 and C-6 to C-9 shown in Table 5 were produced.

Workup

  1. temperatureto reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-bd561cee7e7048ebbdbcb919dd0dc032
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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