O-Toluidine → HCID 21850864, compound

HRID 618445Notes

Reaction equation

HRID 618445 reaction equation
CS(O[C:6]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[N:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)=O.[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(#N)C>[CH3:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][C:6]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[N:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 21850843HCID 21850843, compound

Product 1

HCID 21850864HCID 21850864, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-methanesulfonyloxy-8-methoxy-1,7-naphthyridin-3-carboxylate (261 mg and o-toluidine (0.17 nl) were dissolved into 7 ml of acetonitrile and the solution was heated to reflex for 30 minutes. After cooling the mixture, the solvent was evaporated under reduced pressure and the beside was dissolved into chloroform. The solution was washed with water and then saturated sodium bicarbonate, dried, and concentrate under reduced pressure. The residue was subjected to silica gel column chromatography using a mixture of hexane:ethyl acetate (2:1) as an eluant to give yellow titled compound (180 mg, 67%).

Workup

  1. temperaturethe solution was heated
  2. temperatureAfter cooling the mixture
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe beside was dissolved into chloroform
  5. washThe solution was washed with water
  6. dry with materialsaturated sodium bicarbonate, dried
  7. concentrationconcentrate under reduced pressure
  8. additiona mixture of hexane:ethyl acetate (2:1) as an eluant

Sources & evidence

ORD record
ord-07a148c089904c769dca0eab82d4d03c
Source dataset
uspto-grants-1999_09
Patent number
US05952504

Reaction notes

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