2,6-Pyridinedicarboxylic acid → N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]phthalimide

HRID 2268528Notes

Reaction equation

HRID 2268528 reaction equation
C[O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16]C)=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]3=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]3[C:27]1=[O:36])[CH2:7]2.N1C(C(O)=O)=CC=CC=1C(O)=O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C.O.C(OCC)(=O)C>[CH3:15][O:14][C:10]1[C:9](=[O:16])[C:8]2[CH2:7][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[C:30](=[O:31])[C:29]4=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]4[C:27]3=[O:36])[CH2:5][C:4]=2[C:3](=[O:2])[C:11]=1[O:12][CH3:13]

Participants

7

Reactant 3

HCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrate2×HCID 18348600N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]phthalimide

Product 1

HCID 15552356N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]phthalimideYield 76.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]phthalimide (470 mg), 2,6-pyridinedicarboxylic acid (475 mg), acetonitrile (10 ml), and water (5 ml) was dropwise added a solution of CAN (1.56 g) in acetonitrile (1.5 ml) and water (1.5 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, a solution of CAN (520 mg) in water (2.0 ml) was dropwise added with cooling with ice and stirring was continued for additional 15 min. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=5:1) and then with recrystallization from hexane-ethyl acetate to yield the entitled compound (336 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. stirringstirring
  4. waitwas continued for additional 15 min
  5. washThe organic layer was washed with water and saturated aqueous sodium chloride
  6. customdried
  7. customThe solvent was removed in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=5:1)
  9. customwith recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1970fc22c7ce43089205506e8c978afa
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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