O-Toluidine → HCID 18350675, compound

HRID 1737270Notes

Reaction equation

HRID 1737270 reaction equation
[CH3:1][C:2]1O[C:10](=[O:12])[C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][C:14]1[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(O)(=O)C>[CH3:1][C:2]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:10](=[O:12])[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 22172743HCID 22172743, compound

Product 1

HCID 18350675HCID 18350675, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methyl-3-oxa-1,7-diaza-naphthalen-4-one (1.95 g, 12.0 mmol) was dissolved in acetic acid (30 mL) and o-toluidine (1.92 mL, 18 mmol) was added. The reaction was refluxed 7 hours, cooled and concentrated. The residue was taken up in ethyl acetate and extracted with water, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate and concentrated. The residue was flash chromatographed on silica gel (2×4 inches, packed in hexane) with elution proceeding as follows: 10% ethyl acetate/hexane (500 mL); 25% ethyl acetate/hexane (800 mL); 25% ethyl acetate/hexane (200 mL) and 40% ethyl acetate/hexane (200 mL), unweighed recovered 2-methyl-3-oxa-1,7-diaza-naphthalen-4-one; 40% ethyl acetate/hexane (300 mL), unweighed mixed fraction; 40% ethyl acetate/hexane (3000 mL), 2-methyl-3-o-tolyl-3H-pyrido[3,4-d]pyrimidin-4-one (2.47 g, 81%) of as an off white solid.

Workup

  1. temperatureThe reaction was refluxed 7 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. extractionextracted with water, saturated aqueous sodium bicarbonate, and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed on silica gel (2×4 inches, packed in hexane) with elution proceeding
  8. custom25% ethyl acetate/hexane (200 mL) and 40% ethyl acetate/hexane (200 mL), unweighed recovered 2-methyl-3-oxa-1,7-diaza-naphthalen-4-one

Sources & evidence

ORD record
ord-f2df6431585d40ec959448beac83e38c
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

Loading…