N-(2-naphthylformyl)-N-(5-methylpyridin-2-yl)-2-naphthamide → N-(5-methylpyridin-2-yl)naphthalene-2-carboxamide

HRID 589391Notes

Reaction equation

HRID 589391 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([N:13]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=1)C(C1C=CC2C(=CC=CC=2)C=1)=O)=[O:12]>C(O)C.O.NN>[CH3:32][C:29]1[CH:30]=[CH:31][C:26]([NH:13][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:12])=[N:27][CH:28]=1

Participants

4

Reactant 1

HCID 89590302N-(2-naphthylformyl)-N-(5-methylpyridin-2-yl)-2-naphthamide

Product 1

HCID 7492785N-(5-methylpyridin-2-yl)naphthalene-2-carboxamideYield 98.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

N-(2-naphthylformyl)-N-(5-methylpyridin-2-yl)-2-naphthamide (2.91 g, 6.99 mmol) was dissolved in ethanol (50 mL) and 85% hydrazine hydrate (5 mL), and stirred at room temperature for 8 hours. It was concentrated under reduce pressure, chromatographed on a silica gel column (petroleum ether:ethyl acetate=3:1) to obtain a white solid 1.8 g, at a yield of 98.1%.

Workup

  1. concentrationIt was concentrated
  2. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3b8520bfde694160a823afb5b8f31229
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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