Water → HCID 10568805, compound

HRID 962652Notes

Reaction equation

HRID 962652 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+].Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C)C=O.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:16]3[CH2:15][CH2:14][N:13]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:12][C:11]=3[C:10](=[O:17])[O:9][C:7]=2[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 10568805HCID 10568805, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one (1.5 g, 6.5 mmol), potassium carbonate (0.50 g, 4.7 mmol), and (2-bromethyl)benzene (1.0 mL, 1.4 g, 7.3 mmol) in 10 mL of N,N-dimethylformamide is heated at 900 for 18 hours. The cooled reaction mixture is added to 300 mL of water and 150 mL of ethyl ether. The insoluble material is filtered and washed with fresh ethyl ether. Recrystallization of the solid from aqueous 2-propanol gives 0.60 g (27%) of product; mp 135°-136° C.

Workup

  1. temperatureis heated at 900 for 18 hours
  2. customThe cooled reaction mixture
  3. filtrationThe insoluble material is filtered
  4. washwashed with fresh ethyl ether
  5. customRecrystallization of the solid from aqueous 2-propanol

Sources & evidence

ORD record
ord-0248ad5150b2425ab6bcc105c447b441
Source dataset
uspto-grants-1998_06
Patent number
US05760050

Reaction notes

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