Dimethylformamide → HCID 18803071, compound

HRID 883660Notes

Reaction equation

HRID 883660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].CN(C)C=O.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 60984Methyl bromoacetateHCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 18803071HCID 18803071, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-chloroisatin, compound VIII, (10.0 g, 55.07 mmol) in anhydrous N,N-dimethylformamide (100 ml) potassium carbonate (9.87 g, 71.59 mmol) was added portionwise at 0-5° C. After stirring at 0-5° C. for further 10 minutes and at ambient temperature for one additional hour methyl bromoacetate (8.25 ml, 60.58 mmol) was added dropwise at such a rate that the internal temperature did not exceed 35° C. The resulting orange suspension was allowed to stir at ambient temperature overnight. Water was added (350 ml) and the product was extracted with ethyl acetate (5×100 ml). The combined organic extracts were washed with brine (100 ml), dried (MgSO4) and evaporated under reduced pressure to give the title compound (10.83 g, 76%) as orange solid (HPLC purity 98%). MS (ESI+): 254.1; MS (ESI−): 252.1

Workup

  1. additionwas added dropwise at such a rate that the internal temperature
  2. customdid not exceed 35° C
  3. extractionthe product was extracted with ethyl acetate (5×100 ml)
  4. washThe combined organic extracts were washed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-074c860df26a48909b591997d510330c
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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