Potassium Carbonate → HCID 10570898, compound

HRID 962635Notes

Reaction equation

HRID 962635 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:16]3[CH2:15][CH2:14][NH:13][CH2:12][C:11]=3[C:10](=[O:17])[O:9][C:7]=2[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[N+:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1)([O-:26])=[O:25]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:16]3[CH2:15][CH2:14][N:13]([CH2:31][C:30]4[CH:33]=[CH:34][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=4)[CH2:12][C:11]=3[C:10](=[O:17])[O:9][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 10570898HCID 10570898, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one (1.2 g, 5.2 mmol), potassium carbonate (0.69 g, 5.0 mmol), and 4-nitrobenzyl bromide (1.1 g, 5.1 mmol) in 15 mL of N,N-dimethylformamide is heated at 90° C. for 4 hours. The cooled reaction mixture is evaporated, and the residue partitioned between ethyl acetate and brine. The organic layer is dried (anhydrous magnesium sulfate) and evaporated. Recrystallization of the residue from ethyl acetate gives 0.87 g (47%) of product; mp 176°-178° C.

Workup

  1. customThe cooled reaction mixture
  2. customis evaporated
  3. customthe residue partitioned between ethyl acetate and brine
  4. dry with materialThe organic layer is dried (anhydrous magnesium sulfate)
  5. customevaporated
  6. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-a88ef2e105fe4db6a6f38e2ec1d848f3
Source dataset
uspto-grants-1998_06
Patent number
US05760050

Reaction notes

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