Water → Methyl 2-chloro-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 2277599Notes

Reaction equation

HRID 2277599 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[N:11]=[C:10]([Cl:15])[CH:9]=[CH:8][C:7]=2[CH2:6]1)=[O:4].CC#N.[OH2:19]>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[N:11]=[C:10]([Cl:15])[CH:9]=[CH:8][C:7]=2[C:6]1=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 58155432Methyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 58155423Methyl 2-chloro-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Chloro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid methyl ester (226.7 mg, 1 mmol) was dissolved in CCl4 (3.57 mL) and MeCN (0.357 mL) at room temperature before adding NaIO4 (0.643 g) in 1 mL of H2O, followed by RuCl3.hydrate (62.2 mg). The reaction mixture was stirred vigorously at room temperature for 2 hours. After dilution with DCM, it was filtered through Celite and the filter cake was washed three times with DCM. The combined organic solution was concentrated in vacuo to give a crude product. Flash column chromatography separation (silica gel, 12 g, 20% EtOAc in hexane) then afforded the tile compound (143 mg, 60%) as a white solid. MS: 241.1 (M+H+).

Workup

  1. filtrationAfter dilution with DCM, it was filtered through Celite
  2. washthe filter cake was washed three times with DCM
  3. concentrationThe combined organic solution was concentrated in vacuo
  4. customto give a crude product
  5. customFlash column chromatography separation (silica gel, 12 g, 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-909dd1da8f6c4312a2fe2f5d09654d81
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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