HCID 18785781, compound → HCID 22758828, compound

HRID 1704809Notes

Reaction equation

HRID 1704809 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([CH2:12][CH3:13])[CH2:4][N:3]=1>[Pd].CC1C=CC(C(C)C)=CC=1>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH3:13])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 18785781HCID 18785781, compound

Product 1

HCID 22758828HCID 22758828, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolvent

Procedure

A stirred mixture of (±)-1-amino-4-ethyl-3,4-dihydroisoquinoline (6.83 g.) and 10% palladium on carbon (1.5 g.) in p-cymene (80 ml.) was refluxed for 4 hours. The mixture was filtered and the filtrate reduced to dryness in vacuo to leave an oil which when crystallized successively from Skellysolve B and cyclohexane gave 1.84 g. (27% yield) of the product, m.p. 84°-85°.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationThe mixture was filtered
  3. customto leave an oil which when
  4. customcrystallized successively from Skellysolve B and cyclohexane
  5. customgave 1.84 g

Sources & evidence

ORD record
ord-70f5b368d92b444f96180f4d5122c587
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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