Ethyl Acetate → HCID 178526832, compound

HRID 1976053Notes

Reaction equation

HRID 1976053 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Br:11]Br.C(OCC)(=O)C>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:11][C:7]1[C:2]([OH:1])=[N:3][CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24408Bromine2×HCID 178526703HCID 178526703, compound

Product 1

HCID 178526832HCID 178526832, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

2-Hydroxy-5-nitropyridine (10.0 g, 71 mmol) in chloroform (200 ml) and acetic acid (10 ml) was treated with bromine (3.7 ml, 72 mmol) and then refluxed for 24 hrs. More bromine (3.7 ml, 72 mmol) was added and the mixture refluxed for a further 48 hrs, then cooled. Ethyl acetate (150 ml) was added and the solid formed removed by filtration, washed with ethyl acetate (50 ml) and dried to give the product as an off-white powder (8.5 g).

Workup

  1. temperaturerefluxed for 24 hrs
  2. temperaturethe mixture refluxed for a further 48 hrs
  3. temperaturecooled
  4. customthe solid formed
  5. customremoved by filtration
  6. washwashed with ethyl acetate (50 ml)
  7. customdried

Sources & evidence

ORD record
ord-d7694f28f487456cac1a6f67d51a6557
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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