Pyridine → 2-bromo-n-(2-nitrophenyl)acetamide

HRID 1988798Notes

Reaction equation

HRID 1988798 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[N+:6]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])([O-:8])=[O:7].N1C=CC=CC=1>C(Cl)Cl>[Br:1][CH2:2][C:3]([NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[N+:6]([O-:8])=[O:7])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69462-NitroanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 2207872-bromo-n-(2-nitrophenyl)acetamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Bromoacetyl bromide (173 μL, 1.99 mmol) was added dropwise to a solution of 2-nitroaniline (250 mg, 1.81 mmol) and pyridine (293 μL) in CH2Cl2 (9 mL). The reaction mixture was stirred at room temperature for 45 min. The mixture was then diluted with CH2Cl2 (10 mL), washed with aqueous 1 N HCl solution (10 mL), water (10 ml) and brine (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound (431 mg, 92% yield) as an orange solid.

Workup

  1. washwashed with aqueous 1 N HCl solution (10 mL), water (10 ml) and brine (10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21ef7a1460af4c3ba61e2e003c790649
Source dataset
uspto-grants-2010_01
Patent number
US07642277B2

Reaction notes

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