Hydrochloric Acid → HCID 10857704, compound

HRID 1742881Notes

Reaction equation

HRID 1742881 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.C(=O)(O)[O-].[Na+]>[Fe].C(O)C>[NH2:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([Br:1])[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21190826HCID 21190826, compound

Product 1

HCID 10857704HCID 10857704, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-bromo-4-nitrobenzoate (46g; 0.17 mole), ethanol (250 ml), iron powder (28 g; 0.5 mole) and concentrated hydrochloric acid (20 ml) are successively introduced into a 1 liter flask. The mixture is taken to reflux temperature for four hours. After cooling, the reaction mixture is treated with a saturated solution of sodium bicarbonate (500 ml) and extracted with ethyl acetate (5×300 ml). After drying over magnesium sulphate, filtration and evaporation, ethyl 4-amino-2-bromobenzoate (35.2 g; yield:86%) is isolated, m.p. 93° C. (compound no. 254).

Workup

  1. temperatureto reflux temperature for four hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (5×300 ml)
  4. dry with materialAfter drying over magnesium sulphate, filtration and evaporation

Sources & evidence

ORD record
ord-9b090935c99245598116b2e8e473e81d
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Reaction notes

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