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Hydrochloric Acid → 2-Tert-butyl-4-chloroaniline

HRID 534832
Notes
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Reaction equation

HRID 534832 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[NH:12]C(=O)C)([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>CCO>[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[NH2:12])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18630151HCID 18630151, compound

Product 1

HCID 5175102-Tert-butyl-4-chloroanilineYield 110.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-(2-tert-butyl-4-chlorophenyl)acetamide (Reference Example 18, 4.78 g, 21.2 mmol), concentrated HCl (50 mL) and EtOH (10 mL) was stirred at 110° C. for 5 h. After cooling, the reaction mixture was basified with 8 M NaOH under ice-cooling. The mixture was extracted with ethyl acetate and the organic layer was washed with water, and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (4.29 g) as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. temperaturecooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water, and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05696247048843038986c648ec9e7acd
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853215B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes