Hydrochloric Acid → O-Ethylacetanilide

HRID 1626242Notes

Reaction equation

HRID 1626242 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(OC(=O)C)(=[O:12])C.Cl.N1[CH:23]=[CH:22]C=CC=1>>[CH2:22]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:3][C:1](=[O:12])[CH3:2])[CH3:23]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7670N-EthylanilineHCID 7918Acetic Anhydride

Product 1

HCID 36332O-Ethylacetanilide

Procedure

To the stirred solution of commercially available ethyl aniline (20.3 g, 167.5 mmol, 1 eq.) in anhydrous pyridine (90 mL), 0° C., under argon was added acetic anhydride (32 mL, 335.04 mmol, 2 eq). After the addition, the resulting solution was stirred with warming to room temperature overnight. The reaction solution was cooled (zero degree), pH adjusted between 4 to 5 with 10% HCl, and extracted with ethyl acetate (2×500 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated to provide the title compound as a white solid.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction solution was cooled (zero degree)
  3. extractionextracted with ethyl acetate (2×500 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-287ccd93801b4c16a677f4601c607ab8
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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