Tetrahydrofuran → HCID 18348604, compound

HRID 2268550Notes

Reaction equation

HRID 2268550 reaction equation
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[CH2:12][CH2:13][C:7]=2[C:6]([O:23]C)=[C:5]([O:25][CH3:26])[C:4]=1[O:27][CH3:28].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+]>C(=O)(O)[O-].[Na+].O>[CH3:28][O:27][C:4]1[C:3](=[O:2])[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[CH2:12][CH2:13][C:7]=2[C:6](=[O:23])[C:5]=1[O:25][CH3:26]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348519HCID 18348519, compound

Product 1

HCID 18348604HCID 18348604, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent

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-pyridinone (334 mg), pyridine-2,6-dicarboxylic acid (433 mg), THF (8 ml), and water (4 ml) was added an water (4 ml) solution of CAN (1.89 g) with cooling with ice. After being stirred for 15 min, the reaction mixture was diluted with saturated aqueous sodium bicarbonate 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 recrystallized from diisopropylether to obtain the entitled compound (195 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 recrystallized from diisopropylether

Sources & evidence

ORD record
ord-e6ccd11f390c4bbb9cfed3c9134f9b13
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…