Water → HCID 86670219, compound

HRID 2091606Notes

Reaction equation

HRID 2091606 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]2.[OH2:19]>C(Cl)Cl.CC#N>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[C:8](=[O:19])[N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 962WaterHCID 83844719HCID 83844719, compound

Product 1

HCID 86670219HCID 86670219, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of NaIO4 (9.56 g, 44.7 mmol) and RuCl3 (927 mg, 4.47 mmol) in water (50 mL), DCM (50 mL) and MeCN (2 mL) was added a solution of tert-butyl 6-chloro-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (4.0 g, 14.9 mmol) in DCM (25 mL). This reaction was stirred at room temperature for 2 h. At completion, the reaction was and was quenched with isopropanol (10 mL), filtered over celite and the filter cake was washed with DCM (20 mL). The filtrate was partitioned in a separatory funnel and the layers were separated. The organic layer was extracted with DCM (2×20 mL) and the combined organics were dried over Na2SO4, then filtered and concentrated. The residue was purified by flash chromatography over silica gel (20-50% EtOAc/hexane eluent) to give tert-butyl 6-chloro-1-oxo-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (3.0 g, 71% yield) as a yellow crystalline solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.92 (s, 1H), 7.47 (s, 1H), 4.03 (t, J=6.3 Hz, 2H), 3.09 (t, J=6.1 Hz, 2H), 1.54-1.62 (m, 9H); MS (EI) m/z=283.7 [M+1]+.

Workup

  1. customwas quenched with isopropanol (10 mL)
  2. filtrationfiltered over celite
  3. washthe filter cake was washed with DCM (20 mL)
  4. customThe filtrate was partitioned in a separatory funnel
  5. customthe layers were separated
  6. extractionThe organic layer was extracted with DCM (2×20 mL)
  7. dry with materialthe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography over silica gel (20-50% EtOAc/hexane eluent)

Sources & evidence

ORD record
ord-ed3e875574a34e47bbce34b991b39028
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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