Methanol → 4-Methoxy-3-(2-naphthylethoxy)phenylamine

HRID 431393Notes

Reaction equation

HRID 431393 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[O:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.O.NN.[CH3:27]O>[Ni]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 78934581-Methoxy-2-(naphthylmethoxy)-4-nitrobenzene

Product 1

HCID 699120564-Methoxy-3-(2-naphthylethoxy)phenylamine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

4-Methoxy-3-(2-naphthylethoxy)phenylamine was prepared using the same experimental conditions described in Scheme XII. From 1-methoxy-2-(naphthylmethoxy)-4-nitrobenzene (3.8 g, 12.3 mmol), hydrazine hydrate (3.1 g, 61.4 mmol) and a catalytic amount of Raney nickel in 100 mL of methanol refluxed for 0.5 h., was obtained 3.5 g of product in (100%) yield as a brown oil that crystallized on standing. MS (EI) m/z 279 (M+).

Sources & evidence

ORD record
ord-26a134efc65b4aaa8b54d6040b1b4984
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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