Ammonia → 4-Chloro-N~1~-(propan-2-yl)benzene-1,2-diamine

HRID 1654475Notes

Reaction equation

HRID 1654475 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][CH:7]([CH3:9])[CH3:8])=[C:4]([N+:12]([O-])=O)[CH:3]=1.Cl.N>C(O)C.[Zn]>[NH2:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=1[NH:6][CH:7]([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 27366924-Chloro-2-nitro-N-(propan-2-yl)aniline

Product 1

HCID 27357454-Chloro-N~1~-(propan-2-yl)benzene-1,2-diamineYield 61%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

4-Chloro-N-isopropyl-2-nitroaniline (8 g) was dissolved in ethanol (20 ml) and thereto zinc powder (9.8 g) was added, and concentrated hydrochloric acid (20 ml) was added in portions. The mixture was neutralized with aqueous ammonia and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was distilled (bp 90° C./0.4 mmHg) to give 2-amino-4-chloro-N-isopropylaniline (4.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. distillationThe residue was distilled (bp 90° C./0.4 mmHg)

Sources & evidence

ORD record
ord-3ecb21895aa34071a3424966947fec89
Source dataset
uspto-grants-1995_04
Patent number
US05407936

Reaction notes

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