Acetic Anhydride → Methyl 2-(2-acetamidophenyl)acetate

HRID 1372734Notes

Reaction equation

HRID 1372734 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])([O-])=O.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C1(C)C=CC=CC=1.[Pd]>[C:15]([NH:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 520464Methyl 2-(2-nitrophenyl)acetate

Product 1

HCID 10954745Methyl 2-(2-acetamidophenyl)acetateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Methyl (2-nitrophenyl)acetate (26.6 g, 0.14 mol) and acetic anhydride (51.5 ml, 0.55 mol) were subjected to catalytic hydrogenation for 15 hours in toluene (150 ml) in the presence of 10% Pd/C (53.2% wet, 4.5 g). The reaction mixture was filtered to remove therefrom the catalyst, followed by washing with toluene. The filtrate was distilled under reduced pressure to remove the solvent. The residue was crystallized by the addition thereto of n-hexane and diisopropyl ether. The crystals thus precipitated were collected by filtration, washed with n-hexane, and dried under reduced pressure to give methyl (2-acetamidophenyl)acetate (24.3 g, 84%) as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove
  3. washby washing with toluene
  4. distillationThe filtrate was distilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was crystallized by the addition
  7. customThe crystals thus precipitated
  8. filtrationwere collected by filtration
  9. washwashed with n-hexane
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-92421df2dcf8404bbbb8c6fe9dd0fb5c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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