Sodium periodate → Quinoline-2,4-dicarboxylic acid 4-ethyl ester

HRID 1185439Notes

Reaction equation

HRID 1185439 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([O:9][C:10]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([C:22]2[O:23]C=CC=2)[CH:13]=1)=[O:11])[CH3:8]>ClC(Cl)(Cl)Cl.C(#N)C.O.[Ru](Cl)(Cl)Cl>[CH2:7]([O:9][C:10]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([C:22]([OH:23])=[O:2])[CH:13]=1)=[O:11])[CH3:8]

Participants

7

Reactant 2

HCID 23667635Sodium periodate2×HCID 27000068Ethyl 2-(furan-2-yl)quinoline-4-carboxylate

Product 1

HCID 68599020Quinoline-2,4-dicarboxylic acid 4-ethyl ester

Reagents, catalysts & solvents 4

HCID 61850Ruthenium trichlorideCatalyst2×HCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a vigorously stirred of 8 g of sodium periodate and 20 mg of ruthenium trichloride in 37 ml of tetrachloro-methane, 37 ml of acteonitrile and 54 ml of water 2.5 g of 2-Furan-2-yl-quinoline-4-carboxylic acid ethyl ester was added at RT. Then, after 4 h additional 8 g of sodium periodate and 10 mg of ruthenium trichloride was added and the reaction mixture was stirred for an additional hour. Then, the reaction mixture was diluted with water and extracted with DCM (3×150 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was used in the next reaction step without further purification. Yield: 2.0 g.

Workup

  1. additionwas added at RT
  2. extractionextracted with DCM (3×150 ml)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-7edb90b95b354a24a7c7719081cdc0bd
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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