N,N-Dimethylaniline → HCID 23369617, compound

HRID 1900787Notes

Reaction equation

HRID 1900787 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]2[C:6]=1[C:7]([CH3:18])=[C:8]([CH3:17])[C:9](=[O:16])[NH:10]2)C=C.C(Cl)(Cl)Cl.[OH-].[Na+].CN(C)[C:27]1[CH:32]=CC=C[CH:28]=1>>[CH2:32]([C:14]1[C:5]([OH:4])=[C:6]2[C:11](=[C:12]([CH3:15])[CH:13]=1)[NH:10][C:9](=[O:16])[C:8]([CH3:17])=[C:7]2[CH3:18])[CH:27]=[CH2:28]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 23369786HCID 23369786, compound

Product 1

HCID 23369617HCID 23369617, compound

Conditions

Temperature
200 °C

Procedure

5-Allyloxy-3,4,8-trimethylcarbostyril (1.02 g, 420 mmol) was dissolved in N,N-dimethylaniline (20 ml), and the mixture was stirred in a bath of 200° C. for 2 hours. The reaction mixture was condensed under reduced pressure, to which chloroform and aqueous 2N-NaOH solution were added, then extracted into the aqueous phase. The aqueous phase was neutralized with conc. HCl solution, followed by extracting with chloroform--methanol (10:1), drying, and condensing. The resultant residue was recrystallized from chloroform--methanol--ether. As a result, 989 mg of the title compound was obtained as pale yellow needles (97.0%).

Workup

  1. customcondensed under reduced pressure
  2. extractionextracted into the aqueous phase
  3. extractionby extracting with chloroform--methanol (10:1)
  4. customdrying
  5. customcondensing
  6. customThe resultant residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-7f0163e99f5a419eb7d058169a7660ca
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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