m-Chloroperbenzoic acid → HCID 66656411, compound

HRID 2367723Notes

Reaction equation

HRID 2367723 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[N:10][CH:11]=2)[N:6]=1)=[O:4].ClC1C=C(C=CC=1)C(OO)=[O:20]>ClCCl.CCOC(C)=O.O>[O:20]=[C:11]1[NH:10][CH:9]=[CH:8][C:7]2[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:14]=[CH:13][C:12]1=2

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2761109methyl 1,6-naphthyridine-2-carboxylate

Product 1

HCID 66656411HCID 66656411, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of [1,6]naphthyridine-2-carboxylic acid methyl ester (2.00 g, 10.4 mmol) in DCM (dichloromethane) (50 mL) with mCPBA (m-chloroperoxybenzoic acid) (65%, 3.10 g, 12.0 mmol)) at rt (room temperature) and stir for 2 h. Dilute the reaction mixture with EtOAc and water. Wash the organic layers with sat. NaHCO3 and brine. Extract the organic layer with DCM (4×50 mL) and dry the combined organics over MgSO4, filter and concentrate. Purify the compound by silica gel chromatography eluting with a gradient of 0% to 100% EtOAc/hexanes to obtain the desired product 6-oxy-[1,6]naphthyridine-2-carboxylic acid methyl ester in (930 mg, 4.56 mmol).

Workup

  1. washWash the organic layers with sat. NaHCO3 and brine
  2. extractionExtract the organic layer with DCM (4×50 mL)
  3. dry with materialdry the combined organics over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the compound by silica gel chromatography
  7. washeluting with a gradient of 0% to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-52bf773b8d2845abac57f2f72d723a52
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

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