Ammonia → 4-Aminobenzamide

HRID 450033

Reaction equation

HRID 450033 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH3:11]>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:11])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 177720Benzoyl chloride, 4-amino-

Product 1

HCID 760794-AminobenzamideYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 4-amino-benzoyl chloride (0.38 g, 2.45 mmol) in tetrahydrofuran (2 ml) was added aqueous ammonia solution (15 ml). The reaction mixture was stirred at room temperature for 12 hr. The solvent was removed under vacuum, water added and the compound was extracted into ethyl acetate. The organic layer was dried and concentrated under vacuum. The crude compound was purified using silica gel column chromatography, using chloroform/methanol as eluent, to yield 4-amino-benzamide (0.1 g, 30%).

Workup

  1. customThe solvent was removed under vacuum, water
  2. additionadded
  3. extractionthe compound was extracted into ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated under vacuum
  6. customThe crude compound was purified

Sources & evidence

ORD record
ord-77b9532ce9694d63ae78c3ee0bbc54e6
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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