Phthalic Anhydride → HCID 86590097, compound

HRID 1246614Notes

Reaction equation

HRID 1246614 reaction equation
C1(=O)OC(=[O:5])C2=CC=CC=C12.[Cl:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][N+:16]([O-:5])=[CH:15][C:14]=1[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 86760290HCID 86760290, compound

Product 1

HCID 86590097HCID 86590097, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phthalic anhydride (566 mg, 3.82 mmol) was dissolved in acetonitrile (10 mL) and treated with urea-hydrogen peroxide complex (360 mg, 3.82 mmol) and the suspension was stirred for 15 min. A portion of the Boc-derivative from stage (i) (890 mg, 3.48 mmol) was added and the suspension was stirred at room temperature for 20 h. The residue was partitioned between potassium carbonate solution (100 mL) and DCM (200 mL). The organic layer was separated and the aqueous layer was re-extracted with DCM (3×50 mL). The combined organic fractions were washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography [SiO2; DCM/MeOH/880 NH3 (90:10:1)] afforded the title compound (680 mg, 72%); δH (CDCl3, 300 MHz) 1.42 (9H, s), 2.91 (3H, s), 4.44 (2H, s), 7.23 (1H, d), 8.00 (1H, d), 8.08 (1H, s); MS m/z (TS+) 273 (MH+).

Workup

  1. additiontreated with urea-hydrogen peroxide complex (360 mg, 3.82 mmol)
  2. stirringthe suspension was stirred at room temperature for 20 h
  3. customThe residue was partitioned between potassium carbonate solution (100 mL) and DCM (200 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was re-extracted with DCM (3×50 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to an oil
  9. customPurification by flash chromatography [SiO2; DCM/MeOH/880 NH3 (90:10:1)]

Sources & evidence

ORD record
ord-5c581443663c471cb00027fee5862c73
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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