O-Toluidine → HCID 21850850, compound

HRID 618448Notes

Reaction equation

HRID 618448 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1OS(C)(=O)=O)=[CH:13][CH:12]=[N:11][C:10]=2[O:21][CH3:22])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(#N)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])=[CH:13][CH:12]=[N:11][C:10]=2[O:21][CH3:22])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 21850842HCID 21850842, compound

Product 1

HCID 21850850HCID 21850850, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Butyryl-4-methanesulfonyloxy-8-methoxy-1,7-naphthyridine (259 mg) and o-toluidine (0.17 ml) were dissolved into 7 ml of acetonitrile, and the solution was extracted with chloroform, and the organic phase was washed with water and then saturated sodium bicarbonate. After drying, and concentration under reduced pressure, the resulting residue was subjected to silica gel column chromatography using a mixture of hexane:ethyl acetate (1:1) as an eluant to give yellow titled compound (150 mg, 56%).

Workup

  1. extractionthe solution was extracted with chloroform
  2. washthe organic phase was washed with water
  3. customAfter drying
  4. concentrationconcentration under reduced pressure
  5. additiona mixture of hexane:ethyl acetate (1:1) as an eluant

Sources & evidence

ORD record
ord-0ac973930d8b436b9c4ab5c65627a9df
Source dataset
uspto-grants-1999_09
Patent number
US05952504

Reaction notes

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