Homophthalic anhydride → HCID 12015732, compound

HRID 2302274Notes

Reaction equation

HRID 2302274 reaction equation
[C:1]1(=[O:12])[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.Cl.Cl.[CH3:15][NH:16][NH:17][CH:18]([CH3:20])[CH3:19]>C(O)(=O)C.N1C=CC=CC=1.O>[CH3:15][N:16]1[C:1](=[O:12])[CH2:2][C:3]2[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=2[C:5](=[O:7])[N:17]1[CH:18]([CH3:20])[CH3:19]

Participants

6

Reactant 2

HCID 12801Homophthalic anhydrideHCID 20519798HCID 20519798, compound

Product 1

HCID 12015732HCID 12015732, compoundYield 51.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To the solution of homophthalic anhydride (6.80 g, 41.9 mmol) in 70 mL of glacial acetic acid was added 1-methyl-2-(1-methylethyl)hydrazine, dihydrochloride (6.75 g, 41.9 mmol) in 35 mL of pyridine (Rosen, et al., J. Heterocyclic Chem., 1969, 6, 9-12). The solution was refluxed for 12 h, cooled, diluted with water (300 mL), and extracted with chloroform (3×400 mL). The chloroform extract was washed with 10% hydrochloric acid (600 mL) and 5% sodium bicarbonate (600 mL) , dried over magnesium sulfate and concentrated to dryness. The mixture was purified by silica gel chromatography (hexane/ethyl acetate, 3/1) to afford 2,3,4,5-tetrahydro-3-methyl-2-(1-methylethyl)-1H-2,3-benzodiazepin-1,4-dione (5 g, 51%).

Workup

  1. temperatureThe solution was refluxed for 12 h
  2. temperaturecooled
  3. extractionextracted with chloroform (3×400 mL)
  4. extractionThe chloroform extract
  5. washwas washed with 10% hydrochloric acid (600 mL) and 5% sodium bicarbonate (600 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customThe mixture was purified by silica gel chromatography (hexane/ethyl acetate, 3/1)

Sources & evidence

ORD record
ord-9358071b114f43788ae3167997377c41
Source dataset
uspto-grants-2002_08
Patent number
US06432944B1

Reaction notes

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