Decalin → HCID 58892461, compound

HRID 1886748Notes

Reaction equation

HRID 1886748 reaction equation
O[CH:2]([CH3:21])[CH:3]([NH:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)[C:4]1[CH:9]=[CH:8][C:7](C)=[CH:6][CH:5]=1.[P+3]=O.[CH2:24]1C2C(CCCC2)CCC1>>[CH3:24][C:8]1[CH:9]=[C:4]([C:3]2[C:2]3[C:18](=[CH:17][CH:16]=[C:15]([CH3:19])[CH:21]=3)[C:13]([CH3:14])=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7044DecalinHCID 58892448HCID 58892448, compoundHCID 178526999HCID 178526999, compound

Product 1

HCID 58892461HCID 58892461, compound

Procedure

N-(2-hydroxy-1-p-tolyl-propyl)-3-methylbezamide (2.1 mmol), phosphorus (V) oxide (10 mmol) and decahydronaphtalene (50 mmol) were put in a dried two-neck round-bottom flask. Then, the mixture was stirred at 120 for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and water and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether, and filtered to yield 1-(3-methylphenyl)-4,7-dimethylisoquinoline.

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with dichloromethane and water
  3. distillationdistilled under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography
  5. distillationThe eluate was distilled under reduced pressure
  6. customThe residue was recrystallized from dichloromethane and petroleum ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-86e4393017c04939a8fba7c83a118f84
Source dataset
uspto-grants-2013_08
Patent number
US08501328B2

Reaction notes

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