N-bromobutanimide → 6-(Bromomethyl)phenanthridine

HRID 718738Notes

Reaction equation

HRID 718738 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[N:11]=[C:12]2[C:17](=[C:18]3[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]3)[CH:16]=[CH:15][CH:14]=[CH:13]2>C1C=CC=CC=1>[Br:1][CH2:9][C:10]1[N:11]=[C:12]2[C:17](=[C:18]3[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]3)[CH:16]=[CH:15][CH:14]=[CH:13]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3179886-Methylphenanthridine

Product 1

HCID 856742386-(Bromomethyl)phenanthridineYield 87.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-bromosuccinimide (557 mg, 3.13 mmol) was added to a solution of the phenanthridine 5 (403 mg, 2.09 mmol) in benzene (20 mL) and the reaction mixture was stirred while lit with a tungsten lamp (150 W) for 45 minutes. The reaction crude, including precipitated succinimide, was deposited onto silica and purified by flash chromatography eluting with CH2Cl2. Evaporation of the solvent under reduced pressure yielded the bromo 6 as a white solid (495 mg, 87.1%).

Workup

  1. customThe reaction crude
  2. customincluding precipitated succinimide
  3. custompurified by flash chromatography
  4. washeluting with CH2Cl2
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4db0c1c2e10e4417a053660a0e858854
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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