Dimethylformamide → HCID 135711048, compound

HRID 37489Notes

Reaction equation

HRID 37489 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].CN(C=O)C.P(Cl)(Cl)([Cl:35])=O>>[Cl:35][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([N+:17]([O-:19])=[O:18])=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[N:8]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 178470074HCID 178470074, compound

Product 1

HCID 135711048HCID 135711048, compound

Conditions

Temperature
100 °C

Procedure

In 2.5 ml of phosphorus oxychloride was suspended 130 mg of 3,4-diethoxycarbonyl-2-hydroxy-6-(4-hydroxyphenyl)-5-nitropyridine, whereto 0.4 ml of DMF was added. The mixture was heated at 100° C. for 30 minutes. Then, 0.4 ml of DMF was added and the mixture was heated for further 30 minutes. After the solvent was distilled off, ice-water was added, followed by neutralization with sodium hydrogencarbonate and extraction with ethyl acetate. After the organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried, the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent:ethyl acetate).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated for further 30 minutes
  3. distillationAfter the solvent was distilled off
  4. additionice-water was added
  5. extractionfollowed by neutralization with sodium hydrogencarbonate and extraction with ethyl acetate
  6. washAfter the organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and dried
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-1463a6523746465287afe05d588b267d
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

Loading…