6-Nitroindoline → HCID 22382641, compound

HRID 1372444Notes

Reaction equation

HRID 1372444 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.C(=O)([O-])O.[Na+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CN(C=O)C.CO.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][N:10]2[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 297576-NitroindolineHCID 60984Methyl bromoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 22382641HCID 22382641, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitroindoline (1.0 g, 6.1 mmol) and sodium hydrogen carbonate (0.6 g, 7.1 mmol) in DMF (60 ml) was stirred at room temperature. Methyl bromoacetate (0.68 mL, 1.09 g, 7.1 mmol) was added slowly and the mixture was heated at 90° C. for 1 hour. The mixture was cooled, the solvents evaporated under reduced pressure, and the residue partitioned between ethyl acetate (40 mL) and water (20 mL). The organic layer was dried over MgSO4 and then evaporated to give an orange solid. The solid was dissolved in methanol (100 ml), 5% Pd/C (50 mg, cat.) was added and the suspension was stirred under an atmosphere of hydrogen for 2 hours, during which time the yellow colour disappeared. The catalyst was removed by filtration through celite and the solvent was evaporated to give the amine as a brown oil (0.95 g, 75%).

Workup

  1. temperaturethe mixture was heated at 90° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. customthe solvents evaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate (40 mL) and water (20 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. customto give an orange solid
  8. stirringthe suspension was stirred under an atmosphere of hydrogen for 2 hours, during which time the yellow colour
  9. customThe catalyst was removed by filtration through celite
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c6385ca52fd74a30a62df55673d8176d
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

Loading…