N,N-Dimethylaniline → HCID 23369736, compound

HRID 1900780Notes

Reaction equation

HRID 1900780 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]2)C=C.CN(C)[C:19]1[CH:24]=CC=C[CH:20]=1>CCCCCC>[CH2:24]([C:6]1[C:5]([OH:4])=[CH:14][C:13]([CH3:15])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10](=[O:16])[NH:11]2)[CH:19]=[CH2:20]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 23369721HCID 23369721, compound

Product 1

HCID 23369736HCID 23369736, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
200 °C

Procedure

To 6-allyloxy-8-methylcarbostyril (10.11 (47.0 mmol)), N,N-dimethylaniline (25 ml) was added, and the mixture was stirred in a bath of 200° C. for 11 hours. Subsequently, the mixture was cooled. n-Hexane was added to the cooled mixture. The precipitated crystals were collected by filtration, and were washed with chloroform. The washed material was subjected to a recrystallizing procedure (chloroform--methanol--n-hexane) to obtain 9.36 g of 5-allyl-6-hydroxy-8-methylcarbostyril as colorless needles (92.6%).

Workup

  1. temperatureSubsequently, the mixture was cooled
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwere washed with chloroform

Sources & evidence

ORD record
ord-c6cecc9bced547c5ab758aeab879cdcc
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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