Acetic Acid → HCID 19595128, compound

HRID 612462Notes

Reaction equation

HRID 612462 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[C:6]2=[O:13].Cl.[N:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.C(O)(=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:22]([NH:21][C:18]1[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=1)[C:6]2=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6397485-Methoxy-1,3-dihydro-2-benzofuran-1,3-dioneHCID 223202584-Hydrazinylpyridine hydrochloride

Product 1

HCID 19595128HCID 19595128, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-methoxyisobenzofuran-1,3-dione (33.0 g), 4-pyridinylhydrazine hydrochloride (25.7 g) and glacial acetic acid (100 ml) was heated overnight, under reflux, under nitrogen, with stirring. Water (100 ml) was added, and the mixture was evaporated and dried in vacuo. The residue was triturated with acetone, the acetone decanted, and the residue was triturated with methanol to give 16.1 g of 5-methoxy-2-(4-pyridinylamino)isoindol-1,3-dione. To a mixture of lithium aluminum hydride (6.00 g) and dry tetrahydrofuran (150 ml) at ambient temperature, under nitrogen, 5-methoxy-2-(4-pyridinylamino)isoindol-1,3-dione hydrochloride (16.1 g) was added in portions, with stirring. The reaction mixture was stirred at room temperature, under nitrogen, 4 hrs, and sodium sulfate decahydrate was added in portions. The mixture was filtered through a bed of celite, the filter cake was washed thoroughly with ethyl acetate, and the filtrate was concentrated in vacuo. The residue was chromatographed over silica gel, eluting with 7% methanol-dichloromethane followed by 185:14:1 dichloromethane:methanol:ammomium hydroxide. The appropriate fractions were collected and concentrated. The residue was crystallized from ethanol to give 5.8 (46%) of product, mp 166-167° C.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux, under nitrogen
  3. customthe mixture was evaporated
  4. customdried in vacuo
  5. customThe residue was triturated with acetone
  6. customthe acetone decanted
  7. customthe residue was triturated with methanol

Sources & evidence

ORD record
ord-920ad0cd27a24be1b1a588f5693ad889
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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