2-Methyl-3-nitroaniline → HCID 46736583, compound

HRID 502717Notes

Reaction equation

HRID 502717 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C([O-])(O)=O.[Na+].[Br:17][CH2:18][C:19](Br)=[O:20]>C(Cl)Cl>[Br:17][CH2:18][C:19]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1])=[O:20]

Participants

5

Reactant 3

HCID 117832-Methyl-3-nitroanilineHCID 61147Bromoacetyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 46736583HCID 46736583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-3-nitroaniline (5.0 g, 32.9 mmol) in 120 ml of CH2Cl2 was added 120 ml of saturated NaHCO3 and bromoacetyl bromide (2.85 ml, 6.6 g, 32.9 mmol). The reaction was stirred at room temperature for 64 hours. The layers were separated, and the organic layer was washed with water, brine and then dried over MgSO4. Solvent evaporation afforded 2-bromo-N-(2-methyl-3-nitrophenyl)acetamide as a yellow solid.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customSolvent evaporation

Sources & evidence

ORD record
ord-05c3573577b94daf87b6d8e56a875acb
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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