O-Toluidine → HCID 21850844, compound

HRID 618450Notes

Reaction equation

HRID 618450 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][CH2:22][CH3:23])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:24][C:25]1[C:26]([CH3:31])=[CH:27][CH:28]=[CH:29][CH:30]=1>C(#N)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])=[CH:13][CH:12]=[N:11][C:10]=2[O:21][CH2:22][CH3:23])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 21850863HCID 21850863, compound

Product 1

HCID 21850844HCID 21850844, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Butyryl-8-ethoxy-4-methanesulfonyloxy-1,7-naphthyridine (338 mg) and o-toluidine (214 mg) were dissolved into 7 ml of acetonitrile, and the solution was heated to reflux for 30 minutes and concentrated to evaporate solvent under reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform, and the organic phase was washed with water and then saturated sodium bicarbonate. After dying, and concentration under reduced pressure, the resulting 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 (300 mg, 86%)

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 30 minutes
  3. concentrationconcentrated
  4. customto evaporate solvent under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with chloroform
  7. washthe organic phase was washed with water
  8. concentrationconcentration under reduced pressure
  9. additiona mixture of hexane:ethyl acetate (2:1) as an eluant

Sources & evidence

ORD record
ord-1d1fa48164af4f67b503772a36ae3f50
Source dataset
uspto-grants-1999_09
Patent number
US05952504

Reaction notes

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