1-[2-(5-Fluoro-2-nitrophenoxy)ethyl]naphthalene → HCID 22504195, compound

HRID 1814324Notes

Reaction equation

HRID 1814324 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([CH:20]=1)[O:7][CH2:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>C1COCC1.[Ni]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:21])=[C:6]([O:7][CH2:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH:20]=1

Participants

4

Reactant 1

HCID 225040921-[2-(5-Fluoro-2-nitrophenoxy)ethyl]naphthalene

Product 1

HCID 22504195HCID 22504195, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[2-(5-fluoro-2-nitro-phenoxy)-ethyl]-naphthalene (24.63 g, 79.10 mmol) in THF (200 mL) was shaken with Raney nickel (3.0 g) under H2 (55 psi) for 2 h using Parr apparatus. The reaction mixture was filtered through celite and concentrated. 4-Fluoro-2-(2-naphthalen-1-yl-ethoxy)-phenylamine (21.0 g, 94%) was obtained as a light-yellow solid. 1H NMR (CDCl3, 400 MHz) 8.12 (d, 1H), 7.84 (d, 1H), 7.77 (d, 1H), 7.57-7.42 (m, 4H), 6.60-6.45 (m, 3H), 4.31 (t, 2H), 3.59 (t, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-29fcba0b0f394f65814f2eb71eb4172c
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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