Ethyl 3-(4-cyano-2-nitrophenyl)-2-oxopropanoate → Ethyl 6-cyano-1H-indole-2-carboxylate

HRID 2367728Notes

Reaction equation

HRID 2367728 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=1[N+:15]([O-])=O)[CH3:2]>C(O)(=O)C.O.[Zn]>[CH2:1]([O:3][C:4]([C:5]1[NH:15][C:8]2[C:7]([CH:6]=1)=[CH:12][CH:11]=[C:10]([C:13]#[N:14])[CH:9]=2)=[O:19])[CH3:2]

Participants

5

Reactant 1

HCID 10730167Ethyl 3-(4-cyano-2-nitrophenyl)-2-oxopropanoate

Product 1

HCID 4715002Ethyl 6-cyano-1H-indole-2-carboxylateYield 67.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 3-(4-cyano-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester (1.21 g, 4.62 mmol) in acetic acid (50 mL) and water (8 mL) add zinc powder (1.81 g, 27.7 mmol) portionwise over 2 h. Stir at rt for 3 h then filter to remove the solids. Concentrate the filtrate to a volume of 10 mL, dilute with EtOAc (40 mL), and filter again to remove insoluble material. Concentrate the filtrate to give the desired product 6-cyano-1H-indole-2-carboxylic acid ethyl ester as a solid (670 mg, 3.13 mmol).

Workup

  1. filtrationthen filter
  2. customto remove the solids
  3. concentrationConcentrate the filtrate to a volume of 10 mL
  4. additiondilute with EtOAc (40 mL)
  5. filtrationfilter again
  6. customto remove insoluble material
  7. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-7478494c5e8341ad9b237f148420f9f8
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

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