Acetic Acid → N-(4-bromo-2-methoxy-6-nitrophenyl)acetamide

HRID 539157

Reaction equation

HRID 539157 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH2:11])=[C:4]([O:12][CH3:13])[CH:3]=1.OS(O)(=O)=O.[CH3:19][C:20](O)=[O:21]>CC(OC(C)=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11][C:20](=[O:21])[CH3:19])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 508790564-Bromo-2-methoxy-6-nitroaniline

Product 1

HCID 53491145N-(4-bromo-2-methoxy-6-nitrophenyl)acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-2-methoxy-6-nitrobenzenamine (27.85 g) in HOAc (150 mL) and Ac2O (17 mL) was added conc. H2SO4 at 70° C. and the mixture was stirred at 70° C. for 30 min and kept at rt overnight. The formed precipitate was collected by filtration and washed with hexane to afford the desired product as a light yellow solid (24.45 g, 75%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.01 (s, 3H), 3.92 (s, 3H), 7.61 (d, 1H, J=1.8 Hz), 7.65 (d, 1H, J=1.8 Hz), 9.91 (s, 1H); LC-MS: m/e=289 [M+1]+

Workup

  1. waitkept at rt overnight
  2. filtrationThe formed precipitate was collected by filtration
  3. washwashed with hexane

Sources & evidence

ORD record
ord-8dcc372114854c5fb02d65bfc56b1152
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Linked notes

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