N-bromobutanimide → HCID 70885920, compound

HRID 1050645Notes

Reaction equation

HRID 1050645 reaction equation
[CH3:1][C:2]1([CH3:28])[C:11]2=[CH:12][CH:13]=[CH:14][C:15]3[C:16]([CH3:22])([CH3:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:7]5[C:8]=4[N:9]([C:10]=32)[C:4]2[C:5](=[CH:25][CH:26]=[CH:27][C:3]1=2)[C:6]5([CH3:24])[CH3:23].[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:29][C:19]1[CH:20]=[C:7]2[C:6]([CH3:24])([CH3:23])[C:5]3[CH:25]=[CH:26][CH:27]=[C:3]4[C:2]([CH3:28])([CH3:1])[C:11]5[C:10]6[N:9]([C:4]=34)[C:8]2=[C:17]([C:16]([CH3:21])([CH3:22])[C:15]=6[CH:14]=[CH:13][CH:12]=5)[CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12555372HCID 12555372, compound

Product 1

HCID 70885920HCID 70885920, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (5 g, 13.68 mmol) in CHCl3 (133 mL) at 0° C. was added N-bromosuccinimide (2.44 g, 13.68 mmol) over a period of 20 min. While warming up to room temperature, the resulting solution was stirred in the absence of light overnight. The reaction was quenched with a saturated aqueous solution of Na2S2O3. The resulting mixture was extracted with CH2Cl2 (3×) and the combined organic fractions were dried with MgSO4. After filtration and evaporation of the solvent, the residue was subjected to column chromatography (silica, n-hexane/CH2Cl2 4:1). Final recrystallization from ethanol yielded 2-bromo-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine as a white powder (5.6 g, 92%).

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of Na2S2O3
  2. extractionThe resulting mixture was extracted with CH2Cl2 (3×)
  3. dry with materialthe combined organic fractions were dried with MgSO4
  4. filtrationAfter filtration and evaporation of the solvent
  5. customFinal recrystallization from ethanol

Sources & evidence

ORD record
ord-d0e5fdae29524b579d3375993a288e70
Source dataset
uspto-grants-2016_07
Patent number
US09385326B2

Reaction notes

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