Potassium Carbonate → HCID 19780396, compound

HRID 2081706Notes

Reaction equation

HRID 2081706 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylate

Product 1

HCID 19780396HCID 19780396, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of the indoline (Example 31) (4.39 g), 3-nitrobenzyl bromide (5.02 g) and anhydrous potassium carbonate (3.17 g) in methylethylketone (150 ml) was heated under reflux for 18 hours. On cooling, the inorganics were filtered off and the solvent removed in vacuo. The reaction mixture was extracted from water into ethyl acetate, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with chloroform, gave methyl 1-(3-nitrobenzyl)indoline-5-carboxylate, m.p. 99°-100° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureOn cooling
  4. filtrationthe inorganics were filtered off
  5. customthe solvent removed in vacuo
  6. extractionThe reaction mixture was extracted from water into ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customPurification by flash chromatography on silica
  11. washeluting with chloroform

Sources & evidence

ORD record
ord-c7343b8be8cc42f38d4f9d338644b646
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

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