1,4-Dioxane hydrochloride → 6-Bromo-2,3-dihydro-1,8-naphthyridin-4(1H)-one

HRID 712619Notes

Reaction equation

HRID 712619 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Br:18])=[CH:15][N:16]=2)[C:11](=[O:19])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[Br:18][C:14]1[CH:13]=[C:12]2[C:17](=[N:16][CH:15]=1)[NH:8][CH2:9][CH2:10][C:11]2=[O:19]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117667217HCID 117667217, compound

Product 1

HCID 401522026-Bromo-2,3-dihydro-1,8-naphthyridin-4(1H)-oneYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Bromo-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (628 mg, 1.92 mmol) is dissolved into 3 mL of MeOH and 3 mL of 4 M HCl/1,4-dioxane is added. The mixture is stirred for 16 h and concentrated to dryness. The residue is dissolved into 10 mL CH2Cl2 and 10 mL of H2O and neutralized with saturated aqueous Na2CO3 solution. The aqueous layer is extracted with 2×20 mL of CH2Cl2. The organic phase is dried with MgSO4, filtered and concentrated to give 386 mg of 6-bromo-2,3-dihydro-1H-[1,8]naphthyridin-4-one

Workup

  1. additionis added
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue is dissolved into 10 mL CH2Cl2 and 10 mL of H2O and neutralized with saturated aqueous Na2CO3 solution
  4. extractionThe aqueous layer is extracted with 2×20 mL of CH2Cl2
  5. dry with materialThe organic phase is dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d6d91e898cc844f1a0d688ed34f16bd5
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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