Sulfuric Acid → Ethyl 7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 883878Notes

Reaction equation

HRID 883878 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([Cl:17])=[CH:12][CH:13]=2)[N:8](C(C)(C)C)[CH:7]=1)=[O:5])[CH3:2].S(=O)(=O)(O)O>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([Cl:17])=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86615483HCID 86615483, compound

Product 1

HCID 12804018Ethyl 7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 93.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Conditions

Temperature
70 °C

Procedure

The product from Example 21a (0.282 gm, 0.91 mmol) was combined at room temperature with 2 mL of TFA containing 2 drops of sulfuric acid. The resulting mixture was heated at 70° C. for 16.5 h. The volatiles were removed under vacuum and the residue suspended in water. The product was collected by vacuum filtration, water washed and dried under vacuum to give the title compound as a cream colored solid (0.214 gm, 93%).

Workup

  1. customThe volatiles were removed under vacuum
  2. filtrationThe product was collected by vacuum filtration, water
  3. washwashed
  4. customdried under vacuum

Sources & evidence

ORD record
ord-608ce14115fd44f48792e673871436d8
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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