2-Naphthylamine → HCID 67285131, compound

HRID 1927337Notes

Reaction equation

HRID 1927337 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1.[C:18]1(=O)[CH2:21][CH2:20][CH2:19]1>ClCCl>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[NH:7][C:18]1([C:5]#[N:6])[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 70572-NaphthylamineHCID 14496CyclobutanoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 67285131HCID 67285131, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl cyanide (0.27 ml, 2 mmol) was added dropwise to a mixture of 2-aminonaphthalene (0.143 g, 1 mmol) and cyclobutanone (0.098 g, 1.4 mmol). The reaction mixture was stirred at room temperature for 12 h and then concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane) to yield 13a (0.209 g, 0.94 mmol, 94%) as a yellow solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customto obtain a brown liquid which

Sources & evidence

ORD record
ord-29335cf1b17848928007211fb68dfbe4
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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