N-bromobutanimide → 2-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dione
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])[N:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[N:3]=1Participants
Procedure
A mixture of N-(2-methylpyridin-6-yl)phthalimide (16.7 g), N-bromosuccinimide (15.0 g) and benzoyl peroxide (300 mg) in chloroform (150 ml) was refluxed for 5 hours with stirring under ultraviolet irradiation, and then additional N-bromosuccinimide (12.5 g) and benzoyl peroxide (300 mg) were added thereto. The mixture was further refluxed for 18 hours with stirring under ultraviolet irradiation. The reaction mixture was evaporated to dryness and the residue was extracted with ethyl acetate. The extract was washed with water, dried and evaporated to dryness. The residue was subjected to column chromatography on silica gel eluting with a mixed solvent (toluene:ethyl acetate=20:1) to give N-(2-bromomethylpyridin-6-yl)phthalimide (8.85 g). mp: 169°-170° C.
Workup
- temperaturewas refluxed for 5 hours
- temperatureThe mixture was further refluxed for 18 hours
- stirringwith stirring under ultraviolet irradiation
- customThe reaction mixture was evaporated to dryness
- extractionthe residue was extracted with ethyl acetate
- washThe extract was washed with water
- customdried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-224b375f16f94edc8d8181ced9fa7328
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04591590
Reaction notes
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