Water → ethyl 2-carbazol-9-ylacetate

HRID 476216Notes

Reaction equation

HRID 476216 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].O>CN(C=O)C>[CH:10]1[C:11]2[N:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 2728323ethyl 2-carbazol-9-ylacetateYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution containing carbazole (20 g; 0.12 mol) in DMF (130 ml) was added portionwise sodium hydride (50% suspension) (6.9 g; 0.14 mol); the suspension thus obtained was stirred at room temperature for 30 minutes and then heated to 60° C. A solution containing ethyl 2-bromoacetate (24 g; 0.14 mol) in DMF (20 ml) was added dropwise, and the resulting mixture was stirred for 16 hours. The mixture was poured into H2O (0.5 L) and filtered, and the solid obtained was crystallized from hexane to give ethyl 9H-carbazol-9-ylacetate (20 g).

Workup

  1. customthe suspension thus obtained
  2. temperatureheated to 60° C
  3. additionwas added dropwise
  4. stirringthe resulting mixture was stirred for 16 hours
  5. filtrationfiltered
  6. customthe solid obtained
  7. customwas crystallized from hexane

Sources & evidence

ORD record
ord-076f13a683da4656b3cb1bb6e4892cdf
Source dataset
uspto-grants-2014_01
Patent number
US08637682B2

Reaction notes

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