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

HRID 2197726Notes

Reaction equation

HRID 2197726 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 13a (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-da366b1440fa4dc5b9ee2475d2d6c28f
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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