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

HRID 1278168Notes

Reaction equation

HRID 1278168 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-efc47d8e54434ed28e9794fd7e8a14ce
Source dataset
uspto-grants-1981_07
Patent number
US04280835

Reaction notes

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