HCID 15027234, compound → Methyl 2-acetamido-3-chlorobenzoate

HRID 974414Notes

Reaction equation

HRID 974414 reaction equation
[C:1]([C:5]1[CH:10]=[C:9](Br)[CH:8]=[C:7]([Cl:12])[C:6]=1[NH:13][C:14](=[O:16])[CH3:15])([O:3][CH3:4])=[O:2]>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=1[NH:13][C:14](=[O:16])[CH3:15])([O:3][CH3:4])=[O:2]

Participants

3

Reactant 1

HCID 15027234HCID 15027234, compound

Product 1

HCID 15027235Methyl 2-acetamido-3-chlorobenzoateYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a hydrogenation apparatus was placed 3.1 g of N-(2-carbomethoxy-4-bromo-6-chlorophenyl)acetamide and 100 mL of ethanol. The apparatus was purged with nitrogen and 0.1 g of 10 percent palladium on charcoal was added. The mixture was agitated under a hydrogen atmosphere at 40 psig for 2 hr at ambient temperature. The mixture was filtered to remove the catalyst, and the solvent was removed from the filtrate under reduced pressure. The product was purified by elution from a silica gel column using a gradient of 9:1 to 1:1 methylene chloride : ethyl acetate as the eluent to give 1.8 g of white solid (m.p. 135°-136° C.). 1H NMR (acetoned d6 +CDCl3) δ7.92 (d with fine coupling, 8.0 Hz, lH), 7.74 (d with fine coupling, 8.0 Hz, 1H), 7.46 (t, 8.0 HZ, 1H), 3.98 (s, 3H, OCH3), 2.55 (s, 3H, COCH3).

Workup

  1. customThe apparatus was purged with nitrogen and 0.1 g of 10 percent palladium on charcoal
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. customto remove the catalyst
  5. customthe solvent was removed from the filtrate under reduced pressure
  6. customThe product was purified by elution from a silica gel column

Sources & evidence

ORD record
ord-0d7360e83951429ba36dbb7e1393ef0c
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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