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

HRID 2075848Notes

Reaction equation

HRID 2075848 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].[H][H]>CCO>[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

4

Reactant 2

HCID 10730167Ethyl 3-(4-cyano-2-nitrophenyl)-2-oxopropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 4715002Ethyl 6-cyano-1H-indole-2-carboxylateYield 65.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add to 1.5 g of 3-(4-cyano-2-nitrophenyl)-2-oxopropionic acid ethyl ester, in EtOH (40 mL) 10% Pd/C (0.45 g) and stir under a hydrogen atmosphere until the theoretical amount of hydrogen is absorbed. Filter the mixture and concentrate the filtrate to afford 1.1 g of crude product. Purify by chromatography on SiO2 and elute with CH2Cl2. Concentrate the desired fractions and vacuum dry the residue over night (40° C.) to afford the title compound (0.8 g) as white crystals, mp 176° C.

Workup

  1. customis absorbed
  2. filtrationFilter the mixture
  3. concentrationconcentrate the filtrate
  4. customto afford 1.1 g of crude product
  5. customPurify by chromatography on SiO2
  6. washelute with CH2Cl2
  7. concentrationConcentrate the desired fractions and vacuum
  8. customdry the residue over night (40° C.)

Sources & evidence

ORD record
ord-16e63ce8cb0946c98c1865e69669336d
Source dataset
uspto-grants-2011_04
Patent number
US07923466B2

Reaction notes

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