HCID 66656341, compound → HCID 66656411, compound

HRID 2367724Notes

Reaction equation

HRID 2367724 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:11](=[O:15])[NH:10][CH:9]=[CH:8][C:7]=2[N:6]=1)=[O:4]>C1COCC1.CO>[O:15]=[C:11]1[NH:10][CH:9]=[CH:8][C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13][C:12]1=2

Participants

3

Reactant 1

HCID 66656341HCID 66656341, compound

Product 1

HCID 66656411HCID 66656411, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Stir a solution of 5-oxo-5,6-dihydro-[1,6]naphthyridine-2-carboxylic acid methyl ester (920 mg, 4.51 mmol) in a solution of THF/MeOH/1N LiOH (3:1:1) (30 mL) at rt for 18 h. Concentrate the solution and suspend the residue in water. Treat the solution with AcOH (1 mL) and let sit 1 h until a solid forms. Collect this by filtration to give desired product 5-oxo-5,6-dihydro-[1,6]naphthyridine-2-carboxylic acid (730 mg, 3.84 mmol).

Workup

  1. concentrationConcentrate the solution
  2. additionTreat the solution with AcOH (1 mL)
  3. customCollect this
  4. filtrationby filtration

Sources & evidence

ORD record
ord-72bcdfe4861a4c96b3e7151f84c0e4ce
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

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