Pyridine → 3-Amino-5-cyano-3-(2-ethoxyphenyl)indol-2-one

HRID 1091550Notes

Reaction equation

HRID 1091550 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][CH3:22])O)#[N:2].[N:23]1C=CC=CC=1.O=S(Cl)Cl>C(Cl)Cl.O>[NH2:23][C:6]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH3:22])[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][C:7]1=[O:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 665930415-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one

Product 1

HCID 665930703-Amino-5-cyano-3-(2-ethoxyphenyl)indol-2-oneYield 58.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

8.0 g (27.2 mmol) of intermediate 1b and 43 ml (54.4 mmol) of pyridine were dissolved in 70 ml of methylene chloride. Then, at 0° C., 3 ml (40.8 mmol) of SOCl2 were slowly added dropwise. The reaction mixture was then stirred for a further 30 minutes. The reaction solution was subsequently poured into ice-water, and the organic phase was separated off, washed with water, dried and concentrated in vacuo. This residue was added at 0° C. to a solution of 300 ml of 0.5M NH3 solution in dioxane and 150 ml of methylene chloride. The mixture was stirred at room temperature for 16 h. The reaction solution was concentrated in vacuo, and the residue obtained in this way was suspended in water. The precipitate was separated off and recrystallized from a little methanol. 4.7 g of the product were obtained.

Workup

  1. customthe organic phase was separated off
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. additionThis residue was added at 0° C. to a solution of 300 ml of 0.5M NH3 solution in dioxane and 150 ml of methylene chloride
  6. stirringThe mixture was stirred at room temperature for 16 h
  7. concentrationThe reaction solution was concentrated in vacuo
  8. customthe residue obtained in this way
  9. customThe precipitate was separated off
  10. customrecrystallized from a little methanol

Sources & evidence

ORD record
ord-8f8998385dc44e92bef4062a7a109ba9
Source dataset
uspto-grants-2012_03
Patent number
US08129389B2

Reaction notes

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