Tetrahydrofuran → N,N-Dimethyl-4-[3-(5,6-dimethoxy-4,7-dioxoindan-2-yl)propoxy]benzamide

HRID 2268533Notes

Reaction equation

HRID 2268533 reaction equation
[CH3:1][N:2]([CH3:32])[C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:22][C:21]3[C:16](=[C:17]([O:29]C)[C:18]([O:27][CH3:28])=[C:19]([O:25][CH3:26])[C:20]=3[O:23]C)[CH2:15]2)=[CH:6][CH:5]=1.N1C(C(O)=O)=CC=CC=1C(O)=O.C1COCC1.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+]>O>[CH3:32][N:2]([CH3:1])[C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:22][C:21]3[C:20](=[O:23])[C:19]([O:25][CH3:26])=[C:18]([O:27][CH3:28])[C:17](=[O:29])[C:16]=3[CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348568N,N-Dimethyl-4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzamide

Product 1

HCID 18348583N,N-Dimethyl-4-[3-(5,6-dimethoxy-4,7-dioxoindan-2-yl)propoxy]benzamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a mixture of N, N-dimethyl-4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzamide (700 mg), 2,6-pyridinedicarboxylic acid (792 mg), THF (14 ml), and water (7 ml) was dropwise added a solution of CAN (3.44 g) in water (7 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, water was added to the reaction mixture, which was extracted 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 (438 mg) as crystals.

Workup

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

Sources & evidence

ORD record
ord-d44f106dcf2748eeb2380c23faa306d3
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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