Tetrahydrofuran → HCID 18348675, compound

HRID 2268552Notes

Reaction equation

HRID 2268552 reaction equation
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][C:17]3=[O:26])[CH2:12][CH2:13][C:7]=2[C:6]([O:27]C)=[C:5]([O:29][CH3:30])[C:4]=1[O:31][CH3:32].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][O:31][C:4]1[C:3](=[O:2])[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][C:17]3=[O:26])[CH2:12][CH2:13][C:7]=2[C:6](=[O:27])[C:5]=1[O:29][CH3:30]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348676HCID 18348676, compound

Product 1

HCID 18348675HCID 18348675, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a mixture of 1-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1,2-dihydro-2-quinolinone (612 mg), pyridine-2,6-dicarboxylic acid (702 mg), THF (12 ml), and, water (6 ml) was added an water (6 ml) solution of CAN (3.07 g) with cooling with ice. After being stirred for 15 min, the reaction mixture was diluted with water and 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(hexane to hexane:ethyl acetate=8:1) and then with recrystallization from hexane-ethyl acetate to obtain the entitled compound (310 mg).

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted 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(hexane to hexane:ethyl acetate=8:1)
  7. customwith recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-68a889939ced43c290ed62929e42fe54
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…