1-Chloro-2-[(2-chloroethyl)oxy]-4-nitrobenzene → 4-Chloro-3-[(2-chloroethyl)oxy]aniline

HRID 491609Notes

Reaction equation

HRID 491609 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][Cl:14]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][Cl:14]

Participants

4

Reactant 1

HCID 177561821-Chloro-2-[(2-chloroethyl)oxy]-4-nitrobenzene

Product 1

HCID 177561844-Chloro-3-[(2-chloroethyl)oxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an argon-degassed solution of 1-chloro-2-(2-chloro-ethoxy)-4-nitro-benzene (2.9 g, <12.5 mmol due to contamination) in EtOAc (50 mL) was added 10% by weight Pd/C (1 g). The reaction was stirred under H2 for 18 h then filtered through Celite® and concentrated in vacuo to yield the title compound contaminated by the bromo adduct. MS (MH+)=206.1; Calc'd 206.07 for C8H9Cl2NO.

Workup

  1. filtrationthen filtered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26742fdbdab846dcad31c60332cac6a2
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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