Hydrochloric Acid → HCID 517510, compound

HRID 534832Notes

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]

Participants

5

Reactant 3

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

Product 1

HCID 517510HCID 517510, compoundYield 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
Patent number
US08853215B2

Reaction notes

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