Dimethylformamide → HCID 88351541, compound

HRID 862104Notes

Reaction equation

HRID 862104 reaction equation
[C:1]([O:5]/[N:6]=[C:7](\[OH:24])/[C:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[C:14](=[O:23])[C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[OH:22])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[C:30](Cl)(=O)[C:31](Cl)=O>C1COCC1>[C:1]([O:5]/[N:6]=[C:7](\[O:24][CH2:30][CH3:31])/[C:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[C:14](=[O:23])[C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[OH:22])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178454586HCID 178454586, compound

Product 1

HCID 88351541HCID 88351541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-2-(5-bromo-2-hydroxybenzoyl)nicotinic acid O-t-butyloxime (540 mg) and DMF (0.02 ml) in THF (6 ml) was added, at room temperature, oxalyl chloride (0.33 ml). The mixture was stirred for 2 hours at the same temperature and then concentrated, which was dissolved in THF (2 ml). To the solution was added ethanol (8 ml) at room temperature. The mixture was stirred for 1.5 hour at the same temperature and concentrated. To the concentrate was added water, followed by extraction with ethyl acetate. The extract solution 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 (eluent: ethyl acetate/hexane) to give ethyl(Z)-2-(5-bromo-2-hydroxybenzoyl)nicotinate O-t-butyloxime (403 mg) (Compound 139).

Workup

  1. concentrationconcentrated
  2. dissolutionwhich was dissolved in THF (2 ml)
  3. additionTo the solution was added ethanol (8 ml) at room temperature
  4. stirringThe mixture was stirred for 1.5 hour at the same temperature
  5. concentrationconcentrated
  6. additionTo the concentrate was added water
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract solution was washed with a saturated aqueous saline solution
  9. dry with materialdried (anhydrous sodium sulfate)
  10. concentrationconcentrated
  11. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e2c99b827be24089890c94147013a6ac
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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