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

HRID 1091546Notes

Reaction equation

HRID 1091546 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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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

5

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 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

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-3cc875744e834416adb627209d00f9f1
Source dataset
uspto-grants-2012_03
Patent number
US08129389B2

Reaction notes

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