Sodium Bicarbonate → HCID 131719015, compound

HRID 37487Notes

Reaction equation

HRID 37487 reaction equation
N[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:20][CH:19]=2)[N:3]=1.N([O-])=[O:32].[Na+].C(=O)([O-])O.[Na+]>Cl.O1CCOCC1.O>[CH2:11]([O:10][C:8]([C:7]1[C:2](=[O:32])[NH:3][C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:20][CH:19]=2)=[CH:5][C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH3:12]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 57105554HCID 57105554, compound

Product 1

HCID 131719015HCID 131719015, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In 250 ml of 1N hydrochloric acid and 100 ml of dioxane was dissolved 32.2 g of 2-amino-3,4-diethoxycarbonyl-6-(4-methoxyethoxymethoxyphenyl)pyridine, whereto a solution of 6.9 g (1.3 eq.) of sodium nitrite dissolved in 30 ml of water was added dropwise under ice-cooling. The mixture was stirred for 1 hour and left standing in a refrigerator overnight. The mixture was neutralized with sodium hydrogencarbonate, and dioxane was distilled off, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried. Then, the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent:dichloromethane→ethyl acetate).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. waitleft
  4. customstanding in a refrigerator overnight
  5. distillationwas distilled off
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. customdried
  9. distillationThen, the solvent was distilled off
  10. customThe residue was purified by silica gel column chromatography (eluent:dichloromethane→ethyl acetate)

Sources & evidence

ORD record
ord-13b8ea75399b459d9ff47abf66674903
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

Loading…