HCID 3432930, compound → 2-(2-Chlorophenoxy)aniline

HRID 1464445Notes

Reaction equation

HRID 1464445 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O.[H][H]>O1CCCC1.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15]

Participants

5

Reactant 2

HCID 3432930HCID 3432930, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 125690122-(2-Chlorophenoxy)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-(2-nitrophenoxy)benzene (5.00 g) in tetrahydrofuran (100 mL) was shaken in a Parr Hydrogenator over Raney nickel at 5 psi hydrogen at room temperature for 4 hours. The catalyst was filtered from the reaction, and the solution was evaporated under vacuum to a yellowish oil which crystallized on standing. The solid was crushed, suspended in hexane and filtered to yield the title compound as a light orange solid. Mp: 44°-45° C.

Workup

  1. filtrationThe catalyst was filtered from the reaction
  2. customthe solution was evaporated under vacuum to a yellowish oil which
  3. customcrystallized
  4. customThe solid was crushed
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f4acf4c2855346cbaf1898ef75fb031c
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

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