4-Methoxybenzamide → HCID 10587480, compound

HRID 1597445Notes

Reaction equation

HRID 1597445 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]>ClCCl>[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 dichloromethane 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: 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-c5b7a0343866434580963885a3c597d4
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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