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

HRID 2268529Notes

Reaction equation

HRID 2268529 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][NH:26][C:27](=[O:29])[CH3:28])[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>[CH3:13][O:12][C:11]1[C:3](=[O:2])[C:4]2[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH2:7][C:8]=2[C:9](=[O:16])[C:10]=1[O:14][CH3:15]

Participants

7

Reactant 3

HCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348615N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]acetamide

Product 1

HCID 18348613N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]acetamideYield 76.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]acetamide (700 mg), 2,6-pyridinedicarboxylic acid (857 mg), acetonitrile (7.0 ml), ethyl acetate (7.0 ml), and water (7.0 ml) was dropwise added a solution of CAN (3.75 g) in acetonitrile (3.5 ml) and water (3.5 ml) with cooling with ice. After being stirred for 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 (ethyl acetate) and then with recrystallization from hexane-ethyl acetate) to yield the entitled compound (495 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customwith recrystallization from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1fbbb0fbb3e34e8c80f12d3205c5e1f5
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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