2-Chloro-6-nitroaniline → (2-Amino-3-chlorophenyl)amine

HRID 415127

Reaction equation

HRID 415127 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4]>CO.[Pd]>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 698552-Chloro-6-nitroaniline

Product 1

HCID 3462489(2-Amino-3-chlorophenyl)amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-chloro-6-nitroaniline (1.0 g, 5.81 mmol, commercially available from Apollo International) in methanol (20 mL) was passed through the H-Cube® (Thales Nanotechnology Inc.) operating at 40 bars and ambient temperature with a flow rate of 1 mL/min. The H-Cube® was equipped with a 10% Pd/C cartridge (Catcart™). The reaction mixture was collected and concentrated after being exposed to the hydrogenation conditions. The crude 3-chlorobenzene-1,2-diamine was carried on without further purification. MS (EI): 145 (MH+).

Workup

  1. customoperating at 40 bars and ambient temperature with a flow rate of 1 mL/min
  2. customThe reaction mixture was collected
  3. concentrationconcentrated
  4. customThe crude 3-chlorobenzene-1,2-diamine was carried on without further purification

Sources & evidence

ORD record
ord-a26d6681ebd64b5e8fe0c6f6932def1e
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Linked notes

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