Aniline → HCID 19599218, compound

HRID 1418852Notes

Reaction equation

HRID 1418852 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-])=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)([Cl:25])=O>O1CCCC1.C(N(CC)CC)C.CO.[Pd]>[ClH:25].[C:17]1([NH:16][C:13]([CH2:12][CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 797114-(4-Nitrophenyl)butyric acid

Product 1

HCID 19599218HCID 19599218, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A stirred solution of 4-(4-nitrophenyl)butyric acid (5.0 g; 0.023 moles) in 20 ml of thionyl chloride was refluxed for 4 hours. The solvent was evaporated and the crude acid chloride, 2.5 g, was added dropwise to a stirred solution of aniline (2.0 g; 0.02 moles) in 30 ml of tetrahydrofuran and 10 ml of triethylamine and the reaction was then stirred 18 hours. The triethylamine hydrochloride was removed by filtration and 50 ml of ethyl acetate was added to the organic phase. The organic phase was washed with 1×100 ml of 1N hydrochloric acid and the dried over magnesium sulfate. The solvent evaporated to yield a yellow solid. The solid was dissolved in 100 ml of methanol and 250 mg of 10% palladium on carbon was added, the reaction was hydrogenated over a 4 hour period. The catalyst was removed by filtration and the solvent evaporated. To the residue was added 100 ml of ethyl acetate and hydrochloric acid-gas was added. Upon cooling 4(3-(((phenyl)amino)carbonyl)propyl)aniline hydrochloride, a white solid, crystallized and was collected by filtration to yield 1.7 g.

Workup

  1. customThe solvent was evaporated
  2. customThe triethylamine hydrochloride was removed by filtration and 50 ml of ethyl acetate
  3. additionwas added to the organic phase
  4. washThe organic phase was washed with 1×100 ml of 1N hydrochloric acid
  5. dry with materialthe dried over magnesium sulfate
  6. customThe solvent evaporated
  7. customto yield a yellow solid
  8. waitthe reaction was hydrogenated over a 4 hour period
  9. customThe catalyst was removed by filtration
  10. customthe solvent evaporated
  11. additionTo the residue was added 100 ml of ethyl acetate and hydrochloric acid-gas
  12. additionwas added
  13. temperatureUpon cooling 4(3-(((phenyl)amino)carbonyl)propyl)aniline hydrochloride
  14. customa white solid, crystallized
  15. filtrationwas collected by filtration
  16. customto yield 1.7 g

Sources & evidence

ORD record
ord-6d9271cd17cb4635a0d048c0d4a1c11d
Source dataset
uspto-grants-1999_03
Patent number
US05885985

Reaction notes

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