Azobisisobutyronitrile → HCID 59373107, compound

HRID 1471336Notes

Reaction equation

HRID 1471336 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:12])=[N:4][N:3]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Cl:1])=[N:3][N:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2697331-Chloro-4-methylphthalazine

Product 1

HCID 59373107HCID 59373107, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-chloro-4-methyl-phthalazine (179 mg, 1.00 mmol) and N-bromosuccinimide (187 mg, 1.05 mmol) in CCl4 (4 mL) under argon is added 2,2′-azobisisobutyronitrile (25 mg, 0.15 mmol). The mixture is heated at 90° C. for 2 h. After solvent removal at reduced pressure, the residue is purified on silica gel (25% to 50% ethyl acetate/hexane) to recover 49 mg of 1-chloro-4-methylphthalazine and give 132 mg (51%) of 2 as a light-brown solid, mp 96-98° C. (dec). IR 2861, 1530, 1392, 1285 cm−1; 1H NMR (CDCl3) 5.10 (s, 2H, CH2), 8.01-8.14 (m, 2H, 6,7-PhthH), 8.29 (m, 1H, 5-PhthH), 8.41 (m, 1H, 8-PhthH).

Workup

  1. customAfter solvent removal at reduced pressure
  2. customthe residue is purified on silica gel (25% to 50% ethyl acetate/hexane)
  3. customto recover 49 mg of 1-chloro-4-methylphthalazine

Sources & evidence

ORD record
ord-ef14977b06a34714b32511455907f5c4
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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