p-Chlorophenacyl bromide → HCID 46307188, compound

HRID 1891234Notes

Reaction equation

HRID 1891234 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O.C(=O)([O-])O.[Na+]>C(O)CC>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]2[N:3]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:1]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 1379342-Amino-5-bromo-3-methylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 46307188HCID 46307188, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

1.70 g of 2-amino-5-bromo-3-methylpyridine and 2.13 g of 2-bromo-1-(4-chlorophenyl)ethanone in 75 ml of n-propanol are placed in a round-bottomed flask. 1.08 g of sodium hydrogen carbonate are added. The mixture is heated at 80° C. for 6 h. The reaction mixture is allowed to cool and the solvent is evaporated off under reduced pressure. The residue is taken up between dichloromethane and water, the organic phase is then separated and dried, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. The solid obtained is triturated from diethyl ether and recovered by filtration. 1.7 g of compound are obtained.

Workup

  1. temperatureto cool
  2. customthe solvent is evaporated off under reduced pressure
  3. customthe organic phase is then separated
  4. customdried
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution
  7. customThe solid obtained
  8. customis triturated from diethyl ether
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-0f03fc37a8334c96a200240e8ede7f50
Source dataset
uspto-grants-2013_08
Patent number
US08507520B2

Reaction notes

Loading…