N,N-Dimethylaniline → HCID 23369696, compound

HRID 1900861Notes

Reaction equation

HRID 1900861 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([CH3:17])([CH3:16])[CH2:8][C:9](=[O:15])[NH:10]2)C=C.CN(C)[C:20]1[CH:25]=CC=C[CH:21]=1>>[CH2:25]([C:14]1[C:5]([OH:4])=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:15])[CH2:8][C:7]2([CH3:16])[CH3:17])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 23369778HCID 23369778, compound

Product 1

HCID 23369696HCID 23369696, compoundYield 86.9%

Procedure

5-Allyloxy-4,4-dimethyl-3,4-dihydrocarbostyril (817 mg, 3.73 mmol) was dissolved in dimethylaniline (15 ml), and the resultant solution was stirred in a bath at 205° C. for 5 hours. The reaction solution was condensed under reduced pressure, followed by extracting with chloroform and 2N-aqueous caustic soda solution. The aqueous phase was neutralized with conc. HCl. Subsequently, the neutralized phase was extracted with a mixture of chloroform-methanol (10:1), dried, and condensed under reduced pressure. Recrystallization from a mixture of chloroform-methanol-ether yielded 710 mg of the title compound as pale yellow needles (86.9%).

Workup

  1. customcondensed under reduced pressure
  2. extractionby extracting with chloroform and 2N-aqueous caustic soda solution
  3. extractionSubsequently, the neutralized phase was extracted with a mixture of chloroform-methanol (10:1)
  4. customdried
  5. customcondensed under reduced pressure
  6. customRecrystallization
  7. additionfrom a mixture of chloroform-methanol-ether

Sources & evidence

ORD record
ord-5224e2ff0273437b9454273f85644395
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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