Acetic Acid → HCID 56926084, compound

HRID 330788Notes

Reaction equation

HRID 330788 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C.[Zn]>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[O:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86684782HCID 86684782, compound

Product 1

HCID 56926084HCID 56926084, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Acetic acid (1.068 mL, 18 mmol) was added to the mixture of 25b (600 mg, 1.8 mmol) and zinc dust (1.157 g, 18.0 mmol) in ethanol (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 4 hrs. The mixture was filtered, the solvent distilled off under reduced pressure and the crude was purified by flash column chromatography to obtain the aniline 25c in 84% yield.

Workup

  1. filtrationThe mixture was filtered
  2. distillationthe solvent distilled off under reduced pressure
  3. customthe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-de26211d84ef4f39a152704ee6299ee7
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

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