Sodium Carbonate → HCID 22124621, compound

HRID 1857959Notes

Reaction equation

HRID 1857959 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1.N([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[H+].[B-](F)(F)(F)[F:27]>>[F:27][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acidHCID 22124667HCID 22124667, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22124621HCID 22124621, compoundYield 64%

Procedure

A suspension of (XIII) (1.1 g, 5.8 mmol) in 48% aqueous HBF4 (20 mL) at -10° C. was treated with NaNO2 (0.44 g, 6.38 mmol, added in small portions over 3 hours). The resulting mixture was neutralized (pH 7) with solid Na2CO3 carefully, keeping the temperature below 0° C., and extracted with EtOAc (3×75 mL). The solvent was removed, then chromatography of the residue on silica gel, eluting with ethyl acetate, gave 7-fluoro-1-ethyl-1H-[1,6]naphthyridin-2-one (XV) (0.72 g, 64%).

Workup

  1. customthe temperature below 0° C.
  2. extractionextracted with EtOAc (3×75 mL)
  3. customThe solvent was removed
  4. washchromatography of the residue on silica gel, eluting with ethyl acetate

Sources & evidence

ORD record
ord-84776d2c94b14c1f957a384bc01ce19a
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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