Ethanol → 4-Chloroaniline

HRID 2097364Notes

Reaction equation

HRID 2097364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C23C=CC=CC2C(NC3=O)=O)=[CH:4][CH:3]=1.O.[NH2:27]N.CCO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:27])=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 23132421HCID 23132421, compound

Product 2

HCID 78124-ChloroanilineHCID 23132435HCID 23132435, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[6-(4-Chloro-phenylamino)-hexyl]-phthalimide (3.41 g crude from above, 8.4 mmol) and hydrazine hydrate (2.5 ml, 41.5 mmol) were dissolved in THF (25 mL) and EtOH (25 mL) and stirred under reflux for 21 h. The solvent was removed under reduced pressure, the residue was suspended in THF (50 mL) and the precipitate was filtered off, washed with THF (2×5 mL) and the filtrate was concentrated under reduced pressure to give the title compound together with some 4-Chloroaniline (≈3:2).

Workup

  1. temperatureunder reflux for 21 h
  2. customThe solvent was removed under reduced pressure
  3. filtrationthe precipitate was filtered off
  4. washwashed with THF (2×5 mL)
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9154698a5e044980a48bbb99a4ea5f75
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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