4-Nitro-1H-indole → Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

HRID 74571

Reaction equation

HRID 74571 reaction equation
P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)([O-:12])=[O:11].[O:22]=[C:23](N1CCCC1)[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])O.[Na+]>CO>[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:23](=[O:22])[C:24]([O:26][CH3:27])=[O:25])=[CH:16][NH:17]2)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 1457664-Nitro-1H-indoleHCID 516892Sodium BicarbonateHCID 4432411Diphosphoryl tetrachlorideHCID 10975749Methyl oxo-pyrrolidin-1-yl-acetate

Product 1

HCID 10243717Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.4 mL (68 mmol) diphosphoryl chloride were slowly added dropwise to 10 g (62 mmol) 4-nitroindole and 11 g (68 mmol) methyl oxo-pyrrolidin-1-yl-acetate with stirring and while cooling with ice. The reaction mixture was heated to RT and stirred for 3 h at RT. Then first of all 10 mL MeOH were added dropwise at 0° C. and then saturated sodium hydrogen carbonate solution was added dropwise at 0° C. After repeated extraction with DCM the organic phase was dried and evaporated down to 100 mL. This residue was left to stand at RT and the precipitate formed was suction filtered, washed and dried in the air.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirred for 3 h at RT
  3. extractionextraction with DCM the organic phase
  4. customwas dried
  5. customevaporated down to 100 mL
  6. waitThis residue was left
  7. customto stand at RT
  8. customthe precipitate formed
  9. filtrationfiltered
  10. washwashed
  11. customdried in the air

Sources & evidence

ORD record
ord-68e5f506e7274640bd5fd8e1e106861a
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

Loading…