N-bromobutanimide → Succinimide

HRID 1640711Notes

Reaction equation

HRID 1640711 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:8]2)=[N:3]1.[CH2:15]1[C:20](=[O:21])[N:19]([Br:22])[C:17](=[O:18])[CH2:16]1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:22][CH2:11][C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[CH:5]2.[C:17]1(=[O:18])[NH:19][C:20](=[O:21])[CH2:15][CH2:16]1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 104651492,3-Dimethyl-6-nitro-2H-indazole

Product 2

HCID 11439SuccinimideYield 283.7%HCID 219563503-(bromomethyl)-2-methyl-6-nitro-2H-indazole

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,3-dimethyl-6-nitro-2H-indazole (3.00 g, 15.69 mmol) in CCl4 (500 mL) was added AIBN (0.51 g, 3.14 mmol) and NBS (3.06 g, 17.26 mmol). The mixture was heated to 80° C. for 5 hours then stirred at rt overnight. Approximately half of the solvent was removed in vacuo, and the mixture was filtered. The filtrate was conc. in vacuo, and the crude product was purified by silica gel column chromatography eluting with ethyl acetate and hexane to afford 3-(bromomethyl)-2-methyl-6-nitro-2H-indazole with some succinimide present (4.41 g, 104% TY). 1H NMR (300 MHz, CDCl3) δ 8.68 (d, J=2.1 HZ, 1H), 7.98 (dd, J=9.3, 2.1 Hz, 1H), 7.74 (d, J=9.3 Hz, 1H), 4.87 (s, 2H), 4.28 (s, 3H). MS (ES+, m/z) 270, 272 (M+H).

Workup

  1. customApproximately half of the solvent was removed in vacuo
  2. filtrationthe mixture was filtered
  3. customthe crude product was purified by silica gel column chromatography
  4. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-749fba314972429ba939fd75e39a30a3
Source dataset
uspto-grants-2012_02
Patent number
US08114885B2

Reaction notes

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