Water → Acetamide, N-(2-nitrophenyl)-

HRID 987203Notes

Reaction equation

HRID 987203 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].[C:13](OC(=O)C)(=[O:15])[CH3:14].O>O1CCCC1>[C:13]([NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[N+:3]([O-:5])=[O:4])(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 69462-NitroanilineHCID 7918Acetic AnhydrideHCID 24758Sodium hydride

Product 1

HCID 11090Acetamide, N-(2-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.89 g of sodium hydride (60% content) was suspended in 23.76 g of tetrahydrofuran and cooled with ice. To the obtained suspension, 23.79 g of a tetrahydrofuran solution containing 3.00 g of 2nitroaniline was dropwise added over 1 hour, stirred for 10 minutes, allowed to stand at room temperature and stirred for 30 minutes. To the obtained mixture, 2.41 g of acetic anhydride was added dropwise over 1 hr at room temperature and stirred for 2 hours. Then, water was added to the reaction mixture, and extraction and separation were conducted. The obtained organic layer was analyzed by high performance liquid chromatography to find the yield of the desired product was 84%.

Workup

  1. temperaturecooled with ice
  2. additionwas dropwise added over 1 hour
  3. customto stand at room temperature
  4. stirringstirred for 30 minutes
  5. stirringstirred for 2 hours

Sources & evidence

ORD record
ord-f64fbcae5a8f46a198c8be5cb0f51cc7
Source dataset
uspto-grants-2003_10
Patent number
US06630598B2

Reaction notes

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