Hydrochloric Acid → HCID 178488693, compound

HRID 550776

Reaction equation

HRID 550776 reaction equation
[C:1]([CH:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[Cl:15])[C:4](=O)[CH3:5])#[N:2].O.[NH2:17][NH2:18].Cl>C1(C)C=CC=CC=1.C(O)(=O)C>[NH2:2][C:1]1[NH:18][N:17]=[C:4]([CH3:5])[C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[Cl:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 221781542-(2-Chloro-4-methoxyphenyl)-3-oxobutanenitrile

Product 1

HCID 178488693HCID 178488693, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Under argon gas atmosphere, to a solution of the compound prepared in Example 1 (38.7 g) in toluene, acetic acid (14.5 mL) and 60% aqueous solution of hydrazine hydrate (17.7 mL) were sequentially added at 10 to 30° C. of internal temperature. The mixture was stirred for 7 hours at 45 to 55° C. of internal temperature. To the reaction solution cooled to 10 to 30° C. of internal temperature, 2 mol/L hydrochloric acid was added and then the mixture was separated. The aqueous layer was adjusted to pH 6.5 to 7.5 by adding 25 wt % sodium hydroxide. Isopropyl acetate (216 mL) was added to the adjusted aqueous layer. The separated organic layer was concentrated under reduced pressure. The residue was heated, and n-heptane was added. The solution was cooled to 10 to 30° C. of internal temperature. After the crystal was precipitated, the solution was stirred for 30 minutes. Furthermore, n-heptane was added to the solution, and the mixture was stirred for 1 hour. The precipitated crystal was collected by filtration, dried under reduced pressure for 14 hours or more at about 50° C. to give the title compound having the following physical data (35.5 g (94.8 area %); quantitative value: 61% (2 processes)).

Workup

  1. additionwas added
  2. customthe mixture was separated
  3. additionby adding 25 wt % sodium hydroxide
  4. additionIsopropyl acetate (216 mL) was added to the adjusted aqueous layer
  5. concentrationThe separated organic layer was concentrated under reduced pressure
  6. temperatureThe residue was heated
  7. additionn-heptane was added
  8. temperatureThe solution was cooled to 10 to 30° C. of internal temperature
  9. customAfter the crystal was precipitated
  10. stirringthe solution was stirred for 30 minutes
  11. additionFurthermore, n-heptane was added to the solution
  12. stirringthe mixture was stirred for 1 hour
  13. filtrationThe precipitated crystal was collected by filtration
  14. customdried under reduced pressure for 14 hours or more at about 50° C.

Sources & evidence

ORD record
ord-23cbb45c906a43a8bfaa30078cb036cc
Source dataset
uspto-grants-2011_05
Patent number
US07947697B1

Linked notes

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