Acetone → 3,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzaldehyde

HRID 1739423Notes

Reaction equation

HRID 1739423 reaction equation
C[O:2][CH:3](OC)[C:4]1[C:9]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=2)=[CH:8][C:7]([O:19][CH3:20])=[C:6]([O:21][CH3:22])[CH:5]=1.Cl.CC(C)=O>O>[CH3:22][O:21][C:6]1[CH:5]=[C:4]([C:9]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=2)=[CH:8][C:7]=1[O:19][CH3:20])[CH:3]=[O:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 218408043,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzaldehyde dimethyl acetal

Product 1

HCID 218408403,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzaldehydeYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzaldehyde dimethyl acetal (13.9 g) and 2 M hydrochloric acid (1 ml) are added to a mixture of acetone (30 ml) and water (5 ml), and the mixture is stirred at room temperature for two hours. The mixture is evaporated to remove the acetone, and the remaining aqueous layer is extracted with chloroform. The extract is washed, dried, and concentrated. The residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=4:1) to give 3,4-dimethoxy-6-(2-bromoisonicotinoyl)benzaldehyde (8.65 g).

Workup

  1. customThe mixture is evaporated
  2. customto remove the acetone
  3. extractionthe remaining aqueous layer is extracted with chloroform
  4. washThe extract is washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d71b43967f4e4db4a96ba6b9f56f5a72
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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