2-Methoxyethanol → 5-(2-Methoxyethoxy)naphthalen-2-ylamine

HRID 2070028Notes

Reaction equation

HRID 2070028 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[CH:7][CH:6]=[CH:5]2.[CH3:13][O:14][CH2:15][CH2:16]O.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:13][O:14][CH2:15][CH2:16][O:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([NH2:1])=[CH:3]2

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 902956-AminonaphtholHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 593985605-(2-Methoxyethoxy)naphthalen-2-ylamineYield 219.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Aminonaphthalen-1-ol (100 mg, 0.63 mmol) was dissolved in THF (6 mL), and 2-methoxyethanol (96 mg, 1.26 mmol), DEAD (635 μL, 1.26 mmol), and triphenylphosphine (330 mg, 1.26 mmol) were added thereto. The resulting mixture was stirred at room temperature for 4 hours and then concentrated. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=5:1) to give 5-(2-methoxyethoxy)naphthalen-2-ylamine (300 mg, quantitative) as a wax-like material.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-43ddf9885a6c4165b3a3437e40d8bc37
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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