Ethanol → Ethyl 2-cyano-3-(1-methyl-2-chloro-3-indolyl)acrylate

HRID 1939385Notes

Reaction equation

HRID 1939385 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[C:3]1[Cl:13].CCO.[C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].C(N(CC)CC)C>O>[C:17]([C:19](=[CH:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[Cl:13])[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 53731520Ethyl 2-cyano-3-(1-methyl-2-chloro-3-indolyl)acrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 g of 1-methyl-2-chloroindole-3-carbaldehyde, dissolved in 50 ml of abs. EtOH, was added 2.3 g of ethyl 2-cyanoacetate and 4.2 g of triethylamine. After 19 hours with stirring, the solution was added to 200 ml of water, and the precipitate collected by filtration and dried to give (2a). Yield 2.68 g of (2a), m.p. 131°-132° C.

Workup

  1. filtrationthe precipitate collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-e436ecccadf7426a8c8cc2e4a88a7258
Source dataset
uspto-grants-1997_12
Patent number
US05696148

Reaction notes

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