Homophthalic anhydride → HCID 68746412, compound

HRID 661833Notes

Reaction equation

HRID 661833 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10]1(=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C:12](=[O:20])[O:11]1>C(O)(=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([N:5]2[C:12](=[O:20])[CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]2=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 12801Homophthalic anhydrideHCID 1235383-Bromo-o-toluidine

Product 1

HCID 68746412HCID 68746412, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Step 1 A mixture of 3-bromo-2-methylaniline (1 g, 5.37 mmol) and isochroman-1,3-dione (0.872 g, 5.37 mmol) in acetic acid (15 mL) was heated overnight at 100° C. in a sealed tube. The mixture was cooled to rt and concentrated, and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-bromo-2-methylphenyl)isoquinoline-1,3(2H,4H)-dione as a tan solid (630 mg, 36%). Mass spectrum m/z 330, 332 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated
  3. customthe residue was purified by column chromatography (
  4. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

Sources & evidence

ORD record
ord-91b74d24ddcf4fe58461e27f3f903803
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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