Dimethylformamide → 5-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one

HRID 219755Notes

Reaction equation

HRID 219755 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1([OH:21])[C:18]2[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=2)[NH:12][C:11]1=[O:20])[CH3:2].[CH3:22][N:23](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:22]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:20])[C:10]2([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2])[OH:21])#[N:23]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 574664423-(2-Ethoxyphenyl)-3-hydroxy-5-iodoindol-2-one

Product 1

HCID 665930415-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

37.2 g (94 mMol) of the product 1a and 11.1 g (94 mMol) of zinc cyanide in 300 ml of DMF were heated to 95° C. Then 1.6 g (1.38 mMol) of tetrakis-(triphenylphosphine)palladium(0) were added in portions every 10 minutes. After 45 minutes, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic phase was washed with saturated NaCl solution, dried and concentrated in vacuo. The residue obtained in this way crystallizes from a little ethyl acetate. 24 g of the product were obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated NaCl solution
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained in this way
  6. customcrystallizes from a little ethyl acetate

Sources & evidence

ORD record
ord-f0188d37859e4e628e949453722608ea
Source dataset
uspto-grants-2012_06
Patent number
US08202870B2

Reaction notes

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