N-bromobutanimide → HCID 86617352, compound

HRID 642263Notes

Reaction equation

HRID 642263 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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:33])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:33])[C:9]2[N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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 68428654HCID 68428654, compound

Product 1

HCID 86617352HCID 86617352, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-hydroxy-9-phenyl-9H-b-carboline-3-carboxylic acid ethyl ester (399 mg, 1.20 mmol), NBS (227 mg, 1.26 mmol) and BzOOBz (15 mg, 0.06 mmol) in carbontetrachloride (10 mL) was refluxed for 90 min. Then the reaction was cooled, the mixture was then filtered through a Celite plug, followed by the concentration of filtrate to give the desired product (397 mg). The title compound: ESI MS (m/z): 411 (M+H+).

Workup

  1. temperaturewas refluxed for 90 min
  2. temperatureThen the reaction was cooled
  3. filtrationthe mixture was then filtered through a Celite plug

Sources & evidence

ORD record
ord-d5dc9de99b9b4947ac7071e2721fec97
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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