O-Xylene → HCID 514102, compound

HRID 1973884Notes

Reaction equation

HRID 1973884 reaction equation
[C:1]([OH:13])(=O)[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=O.Cl.[CH3:15][O:16][NH2:17].C1(C)C(C)=CC=CC=1>O>[CH3:15][O:16][N:17]1[C:1](=[O:13])[CH2:2][C:3]2[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5]1=[O:7]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 66643Homophthalic acidHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 514102HCID 514102, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of homophthalic acid (9.0 g., 0.05 mole) and methyoxyamine hydrochloride (4.25 g., 0.05 mole) in 125 ml. of xylene was refluxed for 90 minutes, with water collected in Dean Stark trap as it formed. The reaction mixture was cooled and concentrated by vacuum to one half its original volume, then diluted with ethylacetate, washed with water and dried over sodium sulfate. Recrystallization from isopropanol and ethanol, followed by drying at 100° C. for 4 hours yielded pale pink crystals of 2-methoxyisoquinoline-1,3 (2H, 4H)-dione, m.p. 113°-114° C.

Workup

  1. customcollected in Dean Stark trap as it
  2. customformed
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated by vacuum to one half its original volume
  5. additiondiluted with ethylacetate
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customRecrystallization from isopropanol and ethanol
  9. customby drying at 100° C. for 4 hours

Sources & evidence

ORD record
ord-0a8ee8017679457189646da1f700c588
Source dataset
uspto-grants-1976_12
Patent number
US03998954

Reaction notes

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