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

HRID 487903Notes

Reaction equation

HRID 487903 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, mp 127°-131° C.; MS (m/e) 267 (M+), 238, 161, 150 (100%), 135 and 107. IR (CHCl3) 1671 (C=O), 1614, 1589 and 1566 cm-1. 1H-NMR (CDCl3) delta (ppm): 3.79 (s, OCH3), 5.23 (d, J=1.5 Hz, CH2), 6.86 (d, J=8 Hz, C-8 H), 7.06 (dd, J=8, 2 Hz, C-7 H), 7.37 (d, J=1.5 Hz, vinyl H), 7.36, 7.58, 7.75, 8.52 and 8.57 (multiplets, 5 ArH). Anal. C 71.72, H 4.85, N 5 16, calcd. C 71.90 , H 4.90, N 5.24.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8ed68baaff564c0d9de4b5621149b546
Source dataset
uspto-grants-1994_03
Patent number
US05298512

Reaction notes

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