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

HRID 1654475
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 2736692N1-isopropyl-4-chloro-2-nitroaniline

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702Ethanol
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05407936

Reaction notes

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