4-Fluoroaniline → HCID 11161595, compound

HRID 1818895Notes

Reaction equation

HRID 1818895 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12.[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(O)C>[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]3[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=23)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 11217833HCID 11217833, compound

Product 1

HCID 11161595HCID 11161595, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

8-chloro-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (200 mg, 1.012 mmol) was dissolved in 5 mL of ethanol and then added with 4-fluoroaniline (224.9 mg, 2.024 mmol) and stirred at 80° C. overnight. The mixture was concentrated under reduced pressure. A silica gel column chromatography (20% EtOAc/Hexane) was performed on the resulting residue and 250 mg (90%) of 8-(4-fluoro-phenylamino)-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on was obtained in pale yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7bcb6bb699db4a79ba962e5daf3da1da
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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