Acetic Acid → HCID 23291929, compound

HRID 365517Notes

Reaction equation

HRID 365517 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10]([O-])(=O)[CH3:11].[Na+].[BH4-].[Na+].[OH-].[Na+].[C:19](O)(=O)C>CC(C)=O.C(O)C.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]([CH3:11])[CH3:19])=[CH:4][C:3]=1[CH3:9]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 233594-Bromo-3-methylanilineHCID 517045Sodium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 23291929HCID 23291929, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-bromo-3-methylaniline (5.05 g, 27 mmol) in acetic acid (6.0 mL), acetone (7.0 mL), ethanol (25.0 mL) and water (16.0 mL) was cooled to 0° C. and treated with sodium acetate (7.16 g, mmol). The reaction was stirred 5 minutes and then treated slowly and in several small portions with sodium borohydride (5.15 g, 136 mmol) and the resulting reaction mixture was stirred at 0° C. for 3 hours. The solution was neutralized with NaOH pellets and extracted with ether (2×). The combined organic extracts were washed with brine and dried (Na2SO4). The filtered solution was concentrated under reduced pressure to give the title compound (5.68 g, 92%) as an oil.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at 0° C. for 3 hours
  3. extractionextracted with ether (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4336397a04a40048850e8e85419db51
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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