2-(2-chloro-4-nitrophenoxy)naphthalene → 3-chloro-4-(2-naphthyloxy)aniline

HRID 434612Notes

Reaction equation

HRID 434612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.[H][H]>C1C=CC=CC=1.C(O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[NH2:19]

Participants

6

Reactant 2

HCID 9215882-(2-chloro-4-nitrophenoxy)naphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 34512803-chloro-4-(2-naphthyloxy)anilineYield 60.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

3-Chloro-4-(2-naphthyloxy)nitrobenzene (14.8 g) and platinum dioxide (0.1 g) were suspended in a mixture of benzene and ethanol (1:1) (200 ml), and hydrogenation was carried out until 3.2 liters of hydrogen were absorbed. After removal of the solvent from the reaction mixture by distillation under reduced pressure, the residue was distilled in vacuo to give 3-chloro-4-(2-naphthyloxy)aniline (8 g) as a fraction boiling at 173° to 198° C./0.2 to 0.3 mmHg. M.P., 67°-69° C.

Workup

  1. customwere absorbed
  2. customAfter removal of the solvent from the reaction mixture
  3. distillationby distillation under reduced pressure
  4. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-878d04351c52414c94f0f20873f9c511
Source dataset
uspto-grants-1983_08
Patent number
US04399072

Reaction notes

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