N-bromobutanimide → HCID 22052537, compound

HRID 1937000Notes

Reaction equation

HRID 1937000 reaction equation
[CH2:1]1[CH:13]2[CH:4]([C:5](=[O:14])[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=32)[CH2:3][CH2:2]1.[Br:15]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5](=[O:14])[CH:4]3[CH2:3][CH2:2][CH2:1][CH:13]3[C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 154282261,2,3,3a,5,9b-Hexahydrocyclopenta[c]quinolin-4-one

Product 1

HCID 22052537HCID 22052537, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one (374 mg, 2.0 mmol) in DMF (10 ml) is mixed with N-bromosuccinimide (356 mg, 2.0 mmol). After 15 minutes of stirring at room temperature, the batch is heated for 15 minutes to 100° C., diluted with water and extracted with methyl-tert-butyl ether. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is purified on silica gel with ethyl acetate-hexane: 470 mg (88%) of product.

Workup

  1. temperaturethe batch is heated for 15 minutes to 100° C.
  2. extractionextracted with methyl-tert-butyl ether
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is purified on silica gel with ethyl acetate-hexane

Sources & evidence

ORD record
ord-5987b59fe8e9463c989459e63ad7992c
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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