Triethylamine → HCID 22162180, compound

HRID 1088937Notes

Reaction equation

HRID 1088937 reaction equation
Cl.N[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.C([N:15](CC)CC)C.Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:21]([NH:15][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][CH:11]=2)[CH2:7][C:8]1=[O:12])(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 22162305101389-22-4

Product 1

HCID 22162180HCID 22162180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g. (27.1 mMol) 6-aminoindolin-2-one hydrochloride (Helv. Chim. Acta, 20, 373/1937) are suspended in 100 ml. methylene chloride, mixed with 3.7 ml. (27.1 mMol) triethylamine and stirred for 10 minutes. While cooling with ice, 6.73 g. (37.8 mMol) isonicotinic acid chloride hydrochloride and 5.24 ml. (37.8 mMol) triethylamine are added thereto. After 3 hours, the methylene chloride is distilled off and the residue is worked up with water and filtered with suction. The residue is stirred with hot ethanol. There are obtained 5.6 g. (82% of theory) of the title compound; m.p., 315°-320° C.

Workup

  1. temperatureWhile cooling with ice, 6.73 g
  2. distillationthe methylene chloride is distilled off
  3. filtrationfiltered with suction
  4. customThere are obtained 5.6 g

Sources & evidence

ORD record
ord-942d3f65503645d98e87e696d8ef4a24
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

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