Succinimide → HCID 19972706, compound

HRID 1452307Notes

Reaction equation

HRID 1452307 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[O:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Br:24]N1C(=O)CCC1=O.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:24][CH2:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[O:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 19972541Ethyl 3-methylflavone-8-carboxylate

Product 1

HCID 19972706HCID 19972706, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 9.2 g of ethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate (prepared as described by Da Re et al., J. Med. Chem., 2, 263 (1960)), 6.4 g of N-bromosuccinimide and 0.04 g of benzoylperoxide in 80 ml of anhydrous carbon tetrachloride was stirred at reflux for 1.5 hours. After cooling to room temperature the formed succinimide was collected by suction and washed with cold carbon tetrachloride. The mother liquors were evaporated to dryness in vacuo and the residue was rinsed with diethyl ether and collected by suction yielding 9.2 g of the title compound melting at 133°-134° C. after crystallization from acetone-n-hexane.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customwas collected by suction
  3. washwashed with cold carbon tetrachloride
  4. customThe mother liquors were evaporated to dryness in vacuo
  5. washthe residue was rinsed with diethyl ether
  6. customcollected by suction

Sources & evidence

ORD record
ord-53c993ec95574fd08462258c8e337c5b
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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