N-bromobutanimide → Succinimide

HRID 2265871Notes

Reaction equation

HRID 2265871 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>[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

5

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 1

HCID 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 AlBN (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-9713b26206934f5b8a872b0c570936ac
Source dataset
uspto-grants-2010_12
Patent number
US07858626B2

Reaction notes

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