Hydrochloric Acid → 3,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzoic acid

HRID 1739424Notes

Reaction equation

HRID 1739424 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([Br:20])[CH:15]=2)=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].C1(C=CC=C(O)C=1)[OH:23].Cl[O-].[Na+].Cl>O1CCOCC1.C([O-])(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([Br:20])[CH:15]=2)=[CH:9][C:10]=1[O:11][CH3:12])[C:6]([OH:23])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 218408403,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzaldehydeHCID 23665760Sodium Hypochlorite

Product 1

HCID 218408063,4-Dimethoxy-6-(2-bromoisonicotinoyl)benzoic acidYield 89.6%

Reagents, catalysts & solvents 3

HCID 175AcetateSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,4-dimethoxy-6-(2-bromoisonicotinoyl)benzaldehyde (8.61 g) in dioxane (120 ml) is added dropwise a solution of resorcinol (3.25 g) in acetate buffer (pH 3.8, 60 ml) at room temperature. To the mixture is Gradually added dropwise an aqueous solution of sodium hypochlorite (3.1 g) in water (30 ml), and the mixture is stirred at room temperature for two hours. The pH value of the reaction mixture is adjusted to about pH 1 with conc. hydrochloric acid, and then extracted with chloroform. The extract is washed, dried, and concentrated to give 3,4-dimethoxy-6-(2-bromoisonicotinoyl)benzoic acid (8.07 g).

Workup

  1. extractionextracted with chloroform
  2. washThe extract is washed
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-522548265d3c443e84545689190ffc0b
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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