Triethylamine → HCID 22162180, compound

HRID 979211Notes

Reaction equation

HRID 979211 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-0c5425cc37dd446f8d95c14c2fee0f4a
Source dataset
uspto-grants-1987_05
Patent number
US04666923

Reaction notes

Loading…