3-Nitroaniline → N-(3-aminophenyl)butanamide hydrochloride

HRID 1418850Notes

Reaction equation

HRID 1418850 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-])=O.C(N(CC)CC)C.[C:18]([Cl:23])(=[O:22])[CH2:19][CH2:20][CH3:21].C(O)(C)C.Cl>C1COCC1.CO.[Pd]>[ClH:23].[CH2:19]([C:18]([NH:1][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])=[O:22])[CH2:20][CH3:21]

Participants

8

Reactant 4

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 21912024Isopropanol hydrochloride

Product 1

HCID 19599237N-(3-aminophenyl)butanamide hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-nitroaniline, 5.3 g, 0.038 moles, in 100 ml THF was added 25 ml of triethylamine followed by butyryl chloride. 5.0 g, 0.035 moles. The reaction then was stirred at room temperature for 18 hours. The triethylamine hydrochloride was removed by filtration. To the filtrate was added 100 ml of ethyl acetate, and the organic phase was then washed with 1N hydrochloric acid, 100 ml (twice), and then with 2N sodium hydroxide, 100 ml (twice). The organic phase was dried over magnesium sulfate and the solvent was evaporated to yield an oil. The oil was then dissolved in 100 ml of methanol and 20 ml of isopropanol/hydrochloric acid and to this solution was add 250 mg of 10% palladium on carbon. The reaction was then hydrogenated for 3 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was crystallized from hot isopropanol and ethyl acetate, and was collected by filtration to yield 3-(((propyl)carbonyl)amino)aniline hydrochloride, 2.3 g. The material was used without further purification.

Workup

  1. customThe reaction
  2. customThe triethylamine hydrochloride was removed by filtration
  3. additionTo the filtrate was added 100 ml of ethyl acetate
  4. washthe organic phase was then washed with 1N hydrochloric acid, 100 ml (twice), and then with 2N sodium hydroxide, 100 ml (twice)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customto yield an oil
  8. waithydrogenated for 3 hours
  9. customThe catalyst was removed by filtration
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from hot isopropanol and ethyl acetate
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5fe082f591d94db99573cd863a6f41a2
Source dataset
uspto-grants-1999_03
Patent number
US05885985

Reaction notes

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