1-Chloro-4-(2,6-dichloro-4-nitrophenoxy)naphthalene → 3,5-Dichloro-4-[(4-chloronaphthalen-1-yl)oxy]aniline

HRID 846275Notes

Reaction equation

HRID 846275 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-])=O)=[CH:15][C:14]=2[Cl:23])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:14]([Cl:23])=[CH:15][C:16]([NH2:20])=[CH:17][C:18]=2[Cl:19])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 132459461-Chloro-4-(2,6-dichloro-4-nitrophenoxy)naphthalene

Product 1

HCID 138271123,5-Dichloro-4-[(4-chloronaphthalen-1-yl)oxy]anilineYield 96.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 500 milliliter Parr bottle was charged 4-(4-chloro-1-naphthoxy)-3,5-dichloronitrobenzene (15.84 grams, 42.97 mmol) prepared in Part A and toluene (250 milliliters). The bottle was purged thoroughly with nitrogen and 5% platinum on carbon (0.50 grams) was added immediately following the purge. The reaction mixture was then hydrogenated for 1.5 hours on a rocking Parr hydrogenator at a pressure of 90-100 psi hydrogen at ambient temperature. The reaction mixture was filtered through a pad of celite and the filtrate concentrated under reduced pressure to afford pure 4-(4-chloro-1-naphthoxy)-3,5-dichloroaniline (13.99 grams, 41.31 mmol, 96%) as a white solid having a melting point of 145° C.-147° C. Elemental analysis of the white solid indicated the following:

Workup

  1. customThe bottle was purged thoroughly with nitrogen and 5% platinum on carbon (0.50 grams)
  2. additionwas added immediately
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-071233a560b9425fac9ade998f68daef
Source dataset
uspto-grants-1992_08
Patent number
US05135953

Reaction notes

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