Benzoyl Peroxide → 7-Bromomethyl-4-chlorocinnoline

HRID 1432865Notes

Reaction equation

HRID 1432865 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][N:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 45480238HCID 45480238, compound

Product 1

HCID 540103687-Bromomethyl-4-chlorocinnolineYield 35.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-chloro-7-methylcinnoline (0.6 g, 3.37 mmol) in carbon tetrachloride (30 mL) is treated with N-bromosuccinimide (0.64 g, 3.4 mmol) and a catalytic amount of 70% benzoyl peroxide (0.22 g, 0.63 mmol). The solution is heated to 80° C. overnight, then filtered. The filtrate is concentrated in vacuo and the resulting residue is chromatographed (20% ethyl acetate/methyl chloride) to give the title compound (0.3 g, 1.2 mmol) and some unreacted starting material (0.1 g, 0.56 mmol). MS m/z: [M+H]+=257; 1H NMR (CDCl3, 300 MHz) δ9.35 (s, 1H), 8.55 (s, 1H), 8.2 (d, 1H), 8.85 (d, 1H), 4.75 (s, 2H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customthe resulting residue is chromatographed (20% ethyl acetate/methyl chloride)

Sources & evidence

ORD record
ord-c40b5aec28974a23b59e4aa327dd1569
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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