Anisole → 6,7-Dihydro-2H-pyrano[2,3-c]pyridazin-3(5H)-one

HRID 15149Notes

Reaction equation

HRID 15149 reaction equation
COC1C=CC(C[N:10]2[C:15](=[O:16])[CH:14]=[C:13]3[CH2:17][CH2:18][CH2:19][O:20][C:12]3=[N:11]2)=CC=1.C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[N:11]1[NH:10][C:15](=[O:16])[CH:14]=[C:13]2[CH2:17][CH2:18][CH2:19][O:20][C:12]=12

Participants

4

Reactant 2

HCID 7519AnisoleHCID 675268552-{[4-(Methyloxy)phenyl]methyl}-6,7-dihydro-2H-pyrano[2,3-c]pyridazin-3(5H)-one

Product 1

HCID 675269516,7-Dihydro-2H-pyrano[2,3-c]pyridazin-3(5H)-oneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

2-{[4-(Methyloxy)phenyl]methyl}-6,7-dihydro-2H-pyrano[2,3-c]pyridazin-3(5H)-one (2.75 g, 10.1 mmol) was treated with anisole (10 ml) and TFA (100 ml) and heated at 70° C. for 24 hours. The solution was cooled and evaporated and the residue taken up in 2.5% methanol/dichloromethane. This was applied to a silica gel column, and then elution with this solvent mixture followed by 5% methanol/dichloromethane gave the product as an off white solid (1.36 g, 88%).

Workup

  1. temperatureThe solution was cooled
  2. customevaporated
  3. washelution with this solvent mixture

Sources & evidence

ORD record
ord-09883fb592414b65901aa8c579eb0af8
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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