Pyridine → N-((4-Nitrophenyl)methyl)acetamide

HRID 552120Notes

Reaction equation

HRID 552120 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1)([O-:4])=[O:3].N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:12][C:19](=[O:21])[CH3:20])=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 41784N-((4-Nitrophenyl)methyl)acetamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8.0 g (42 mmol, 1.0 eq.) of (4-nitrophenyl)methanamine hydrochloride in 40 mL of methylene chloride and 28 mL (340 mmol, 8.0 eq.) of pyridine was added 16 mL (170 mmol, 4.0 eq.) of acetic anhydride. The mixture was stirred at room temperature for 16 h and diluted with 200 mL of methylene chloride. The organic solution was washed with sat. brine and dried (Na2SO4). The solvent was removed in vacuo to provide 8.0 g (41 mmol, 98%) of N-(4-nitrobenzyl)acetamide (I-21).

Workup

  1. washThe organic solution was washed with sat. brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ef5a8c3bb1414f3dba26f12570d19729
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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