Acetic Anhydride → HCID 21310736, compound

HRID 583182Notes

Reaction equation

HRID 583182 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[NH2:13].[C:14](OC(=O)C)(=[O:16])[CH3:15]>CC(O)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[NH:13][C:14](=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70991182-bromo-6-methoxy-4-nitroaniline

Product 1

HCID 21310736HCID 21310736, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 23 g of 2-bromo-6-methoxy-4-nitrophenylamine in 125 mL of acetic anhydride and 100 mL of AcOH was refluxed at 110° C. Following reflux for 5 h, mixture was dumped into 1.5 L of ice water. A precipitate formed, and was collected via filtration. The precipitate was then placed in EtOH and refluxed for 15 min. 9 mL of conc. NH4OH was then added to the hot mixture. The solution was then cooled, and a precipitate formed and collected again via filtration. The solid was washed with ethanol(2×) and ether, and allowed to air dry. 21.5 g of title compound as a tan powder was collected.

Workup

  1. temperatureFollowing reflux for 5 h
  2. customA precipitate formed
  3. filtrationwas collected via filtration
  4. temperaturerefluxed for 15 min
  5. addition9 mL of conc. NH4OH was then added to the hot mixture
  6. temperatureThe solution was then cooled
  7. customa precipitate formed
  8. filtrationcollected again via filtration
  9. washThe solid was washed with ethanol(2×) and ether
  10. customto air dry
  11. custom21.5 g of title compound as a tan powder was collected

Sources & evidence

ORD record
ord-ebfeb554c4fa4d4789fcb8f2671b2900
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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