Hydrochloric Acid → HCID 23329122, compound

HRID 225162Notes

Reaction equation

HRID 225162 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][C:4]=1[N+:16]([O-])=O>[Fe]>[NH2:16][C:4]1[CH:5]=[C:6]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:3]=1[Br:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19989839HCID 19989839, compound

Product 1

HCID 23329122HCID 23329122, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

3.6 ml of concentrated HCl are added dropwise to a mixture of 10 g of 4-(4-bromo-3-nitrophenyl)-4-oxobutanoic acid and 6.5 g of iron powder, the mixture is then boiled under a reflux condenser for 4 hours and undissolved material is filtered off hot. The filtrate is evaporated and, after adding water and 5 ml of 2 N HCl, the oily residue is extracted with ethyl acetate and, after drying the organic phase over sodium sulfate, the solvent is distilled off. Colorless crystalline 4-(3-amino-4-bromophenyl)-4-oxobutanoic acid is obtained, melting point 169°-171° (from water/glacial acetic acid).

Workup

  1. filtrationundissolved material is filtered off hot
  2. customThe filtrate is evaporated
  3. additionafter adding water and 5 ml of 2 N HCl
  4. extractionthe oily residue is extracted with ethyl acetate
  5. dry with materialafter drying the organic phase over sodium sulfate
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-9f9b65d768e7434eabc323e65059863e
Source dataset
uspto-grants-1980_11
Patent number
US04235918

Reaction notes

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