Sodium Bicarbonate → 3-(Trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 1896934Notes

Reaction equation

HRID 1896934 reaction equation
[O:1]=[C:2]1[N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9][C:8]2[N:7]=[CH:6][C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][C:3]1=2.C(=O)(O)[O-].[Na+]>ClCCl.C(O)(C(F)(F)F)=O>[F:21][C:19]([F:20])([F:22])[C:5]1[CH:6]=[N:7][C:8]2[CH2:9][CH2:10][NH:11][C:2](=[O:1])[C:3]=2[CH:4]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58562753tert-butyl 5-oxo-3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 585627773-(Trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Into a 100 mL round-bottom flask, was placed a solution of tert-butyl 5-oxo-3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (as prepared in the previous step, 2.7 g, 8.54 mmol, 1.00 equiv) in dichloromethane (20 g) and CF3COOH (4 g). The reaction mixture was stirred for 2 h at room temperature. The pH value of the solution was adjusted to 8 with sodium bicarbonate. The resulting solution was extracted with 3×30 mL of dichloromethane, and the combined organic layers was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The title compound was obtained a yellow solid.

Workup

  1. customInto a 100 mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×30 mL of dichloromethane
  3. washthe combined organic layers was washed with 1×50 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a7575e84878c4eb2bffb5257a563436b
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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