HCID 15907523, compound → HCID 15907524, compound

HRID 651401Notes

Reaction equation

HRID 651401 reaction equation
[Cl:1][C:2]1[C:12]([Br:13])=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>Cl.C(O)C.[Cl-].[Na+].O.[Fe]>[Cl:1][C:2]1[C:12]([Br:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 1

HCID 15907523HCID 15907523, compound

Product 1

HCID 15907524HCID 15907524, compoundYield 88.5%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

2.25 kg (7.3 mol) of ethyl 2-chloro-3-bromo-5-nitrobenzoate was dissolved in a mixture comprising 4000 ml of concentrated hydrochloric acid and 4000 ml of ethanol. 1 kg of powdered iron was added to the obtained solution in portions so as to maintain the bulk temperature at 80° C. The reaction mixture was cooled, followed by the addition of a saturated brine. The resulting mixture was extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure to give 1.8 kg of the title compound as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bddacf681004075ae23ff4e79775e5b
Source dataset
uspto-grants-2001_08
Patent number
US06281214B1

Reaction notes

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