4-Methoxybenzamide → HCID 10587480, compound

HRID 2300597Notes

Reaction equation

HRID 2300597 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.Br[CH:13]([CH3:21])[C:14](=O)[CH2:15][C:16]([O:18][CH3:19])=[O:17]>C(Cl)Cl>[CH3:19][O:18][C:16](=[O:17])[CH2:15][C:14]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:8][C:13]=1[CH3:21]

Participants

4

Reactant 2

HCID 769594-MethoxybenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 10587480HCID 10587480, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 725 mg (4.80 mmol) of 4-methoxybenzamide and 1.0 g (4.80 mmol) of methyl 4-bromo-3-oxo-pentanoate was heated neat at 120° C. for 2 h. The resulting dark slurry was cooled to RT, diluted with 2 mL of DCM and purified by silica gel flash column chromatography using hexane/EtOAc (3/1) as eluent to afford 189 mg of the title compound as a yellow solid: 1H NMR (CDCl3, 400 MHz) δ7.92 (d, 2H, J=8.9), 6.93 (d, 2H, J=8.9), 3.85 (s, 3H), 3.73 (s, 3H), 3.56 (s, 2H), 2.34 (s, 3H); low resolution MS (FAB)m/e 285 (MH+), 284 (M+).

Workup

  1. temperatureThe resulting dark slurry was cooled to RT
  2. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-b8a798fdec624dc1ae811dbd1da41426
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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