Hydrochloric Acid → 2-Chloro-4-butylaniline

HRID 1925713Notes

Reaction equation

HRID 1925713 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[C:7]([Cl:15])[CH:6]=1)[CH2:2][CH2:3][CH3:4].Cl.[OH-].[K+]>C(O)C>[Cl:15][C:7]1[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:10]=[CH:9][C:8]=1[NH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59180380N-(4-butyl-2-chlorophenyl)acetamide

Product 1

HCID 211613422-Chloro-4-butylanilineYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 68 (8.54 g; 37.9 mmol) in ethanol (20 mL) was added concentrated hydrochloric acid (20 mL). The resulting mixture was heated at 120° C. for 5 hours, allowed to cool to room temperature, then made basic with aqueous potassium hydroxide, and extracted with methyl tert-butyl ether (3×75 mL). The combined organic extracts were washed with aqueous saturated sodium chloride, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title product as a dark oil (5.89 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with methyl tert-butyl ether (3×75 mL)
  3. washThe combined organic extracts were washed with aqueous saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2a1e8f0751c24a8d88eed05c66fad08d
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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