O-Xylene → HCID 21490703, compound

HRID 1973891Notes

Reaction equation

HRID 1973891 reaction equation
[C:1]([OH:13])(=O)[CH2:2][CH:3]1[CH:11]=[CH:10][CH2:9][CH2:8][CH:4]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[CH2:11][CH2:10][CH2:9][CH2:8][C:4]=2[C:5]1=[O:7]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 131710580HCID 131710580, compound

Product 1

HCID 21490703HCID 21490703, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tetrahydrohomophthalic acid (9.2 g., 0.05 mole) and methoxyamine hydrochloride (4.25 g., 0.05 mole) in 125 ml. of xylene is refluxed for 90 minutes, with water collected in Dean Stark trap as it formed. The reaction mixture is cooled and concentrated by vacuum to one-half its original volume, then diluted with ethyl acetate, washed with water and dried over sodium sulfate. Recrystallization from isopropanol and ethanol, followed by drying at 100° C. for 4 hours yields 2-methoxy-5,6,7,8-tetrahydroisoquinoline-1,3(2H,4H)-dione.

Workup

  1. customcollected in Dean Stark trap as it
  2. customformed
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated by vacuum to one-half its original volume
  5. additiondiluted with ethyl acetate
  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-8937c517d30b4b6fb92ef2d4e2e7e9af
Source dataset
uspto-grants-1976_12
Patent number
US03998954

Reaction notes

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