Formic Acid → N-(4-chlorophenyl)formamide

HRID 1809204Notes

Reaction equation

HRID 1809204 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9](O)=[O:10]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:9]=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 78124-Chloroaniline

Product 1

HCID 17475N-(4-chlorophenyl)formamideYield 97%

Procedure

4-Chloroaniline (15 g, 117 mmol) and formic acid (25 mL, 663 mmol) were heated to reflux for 2 hours. The mixture was concentrated in vacuo. Saturated aqueous sodium hydrogen carbonate was added and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo to give N-(4-chloro-phenyl)-formamide (17.6 g, 97%) as a grey crystalline compound.

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionSaturated aqueous sodium hydrogen carbonate was added
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2ea66b1f6e247018088da3310957288
Source dataset
uspto-grants-2013_01
Patent number
US08362024B2

Reaction notes

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