3-Pyridinecarboxaldehyde → 6-Methoxy-3-(3-pyridyl)methylene-4-chromanone

HRID 610352Notes

Reaction equation

HRID 610352 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[O:13].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.N1CCCC1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C:7](=[CH:20][C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)[C:6]2=[O:13]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 31268PyrrolidineHCID 46121686-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 538130796-Methoxy-3-(3-pyridyl)methylene-4-chromanoneYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a 25° C. mixture of 20.0 g (0.112 mol) of 6-methoxy-4-chromanone and 18.09 g (0.169 mol) of 3-pyridinecarbaldehyde in 100 ml of methanol was added 14.1 ml (0.169 mol) of pyrrolidine. The resultant solution was allowed to stir 60 hours at 25° C., cooled to 0° C. and filtered to yield 17.07 g (57%) of the title compound, m.p. 127-131° C.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationfiltered

Sources & evidence

ORD record
ord-3b31463d8e9144f8a714605beb63170c
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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