Acetic Acid → 5-Bromo-6-ethoxy-1,7-naphthyridin-8-amine

HRID 1881762Notes

Reaction equation

HRID 1881762 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[N:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].C(O)(=O)C.[Br:19]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:19][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[N:13][C:12]([NH2:14])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 516892Sodium BicarbonateHCID 130013416-Ethoxy-1,7-naphthyridin-8-amine

Product 1

HCID 591431045-Bromo-6-ethoxy-1,7-naphthyridin-8-amineYield 65.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 250 mL round bottom flask was added 6-ethoxy-1,7-naphthyridin-8-amine (0.65 g, 3.43 mmol), glacial acetic acid (20 mL), followed by the dropwise addition of bromine (0.60 g, 3.78 mmol) dissolved in carbontetrachloride (40 mL). After addition was complete, the mixture was stirred for 2 h then neutralized with saturated NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The resultant residue was purified by silica gel to yield 5-bromo-6-ethoxy-1,7-naphthyridin-8-amine as a pale yellow solid (0.6 g, 2.24 mmol, 65%). 1H NMR (400 MHz, CDCl3): δ ppm 8.53 (d, J=3.95 Hz, 1H), 8.22 (d, J=8.79 Hz, 1H), 7.50 (dd, J=8.57, 4.17 Hz, 1H), 5.87 (br. s., 2H), 4.48 (q, J=7.03 Hz, 2H), 1.44 (t, J=7.03 Hz, 3H). LC/MS m/z 270 [M+H].

Workup

  1. additionAfter addition
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resultant residue was purified by silica gel

Sources & evidence

ORD record
ord-94b5f109a1b6461993afaa349a8275d0
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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