Indole → HCID 53814688, compound

HRID 904010Notes

Reaction equation

HRID 904010 reaction equation
Br[CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.[OH-].[Na+]>C1C=CC=CC=1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:13]1([CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

7

Reactant 3

HCID 798IndoleHCID 14798Sodium HydroxideHCID 69637Diethyl bromomalonate

Product 1

HCID 53814688HCID 53814688, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of diethyl 2-bromomalonate (0.15 m) and indole (0.1 m) in 100 ml of benzene is added a solution of sodium hydroxide (0.1 m) in water. To this mixture is added tetra-n-butylammonium bromide (0.5 mmole). This mixture is stirred at about 25° C. for 16 hours. The phases are separated, the organic phase is dried and evaporated to give diethyl (1H-indol-1-yl)malonate.

Workup

  1. customThe phases are separated
  2. customthe organic phase is dried
  3. customevaporated

Sources & evidence

ORD record
ord-1ded3fecd1744f16a6716242c0ea01bc
Source dataset
uspto-grants-1980_10
Patent number
US04229574

Reaction notes

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