Benzoyl Peroxide → N-[5-(bromomethyl)pyridin-2-yl]-2-naphthamide

HRID 589392Notes

Reaction equation

HRID 589392 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[O:10])=[N:6][CH:7]=1.[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 7492785N-(5-methylpyridin-2-yl)naphthalene-2-carboxamide

Product 1

HCID 89590303N-[5-(bromomethyl)pyridin-2-yl]-2-naphthamideYield 38.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-(5-methylpyridin-2-yl)-2-naphthamide (1.31 g, 5.0 mmol), N-bromosuccinimide (0.89 g, 5.0 mmol) and benzoyl peroxide (0.12 g, 0.5 mmol) were dissolved in carbon tetrachloride (50 mL), and reacted under protection of nitrogen for 16 hours. It was filtered while hot, and the filter cake was washed with carbon tetrachloride. The filtrate was concentrated, chromatographed on a silica gel column (petroleum ether:ethyl acetate=5:1) to obtain a white solid 0.66 g, at a yield of 38.6%.

Workup

  1. customreacted under protection of nitrogen for 16 hours
  2. filtrationIt was filtered while hot, and the filter cake
  3. washwas washed with carbon tetrachloride
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b2879721d78e4f39965a29e29d242382
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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