Hydrochloric Acid → 2-(3-Methylbutyl)aniline

HRID 1416537Notes

Reaction equation

HRID 1416537 reaction equation
CO.[CH3:3][CH:4]([CH3:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O.Cl.C(=O)([O-])O.[Na+]>O>[CH3:3][CH:4]([CH3:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 184176902-(3-Methylbutyl)nitrobenzene

Product 1

HCID 187640942-(3-Methylbutyl)anilineYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture composed of 10 ml of methanol, 1.3 g (6.4 mmol) of the above 2-(3-methylbutyl)nitrobenzene, and 6.4 ml of concentrated aqueous hydrochloric acid solution, 1.4 g (25.1 mmol) of reduced iron was added in portions and heated to 60° C. with stirring for 1 hour. The reaction mass was poured into water, neutralized with a saturated aqueous sodium hydrogen carbonate solution and filtered to remove precipitated iron hydroxide. The filtrate was extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.95 g of the desired product as oil. Yield was 85%.

Workup

  1. additionwas added in portions
  2. filtrationfiltered
  3. customto remove
  4. customprecipitated iron hydroxide
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d793bc36ff3a486a9f8da9f328e57668
Source dataset
uspto-grants-1999_06
Patent number
US05914344

Reaction notes

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