N-bromobutanimide → HCID 86617365, compound

HRID 642419Notes

Reaction equation

HRID 642419 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10]([CH3:20])[C:11]3[C:16]([C:17]=2[C:18]=1[OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].C1C(=O)N([Br:28])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:28])[C:9]2[N:10]([CH3:20])[C:11]3[C:16]([C:17]=2[C:18]=1[OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68426685HCID 68426685, compound

Product 1

HCID 86617365HCID 86617365, compoundYield 117.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-hydroxy-9-methyl-9H-beta-carboline-3-carboxylic acid ethyl ester (511 mg), NBS (354 mg), and BzOOBz (12.7 mg) in carbon tetrachloride (20 mL) was refluxed for 25 min; then cooled, solvents were removed, the residue was purified with column to give the title compound (773 mg). ESI MS (m/z): 349 (M+H)+.

Workup

  1. temperaturewas refluxed for 25 min
  2. temperaturethen cooled
  3. customsolvents were removed
  4. customthe residue was purified with column

Sources & evidence

ORD record
ord-b00b29ae252f4e438f1c5ca1a95bbf3e
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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