3,4,5,6-Tetrahydrophthalic anhydride → HCID 68997521, compound

HRID 1821382Notes

Reaction equation

HRID 1821382 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.[C:19]1(=O)[C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[C:21](=[O:28])[O:20]1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[C:19](=[O:20])[C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[C:21]2=[O:28])=[N:2]1

Participants

5

Reactant 3

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 516892Sodium BicarbonateHCID 69001756HCID 69001756, compound

Product 1

HCID 68997521HCID 68997521, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of Compound 2 (50 mg, 0.21 mmol) in acetic acid (1.0 mL), 4,5,6,7-tetrahydroisobenzofuran-1,3-dione (39 mg, 0.26 mmol) was added followed by heating under reflux for 1.0 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10) and crystallized from ethyl acetate to obtain Compound 203 (37 mg, 46%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.0 hour
  3. extractionextracted with ethyl acetate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-946f775442794bfbac8c1420f11f1881
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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