Sodium → HCID 10727124, compound

HRID 2292120Notes

Reaction equation

HRID 2292120 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[Na]>>[C:12]1([CH:4]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:2][NH:3]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 5360545Sodium2×HCID 119836901-chloro-3-phenylisoquinoline

Product 1

HCID 10727124HCID 10727124, compoundYield 106.4%

Procedure

1-Chloro-3-phenylisoquinoline (2.8 g) was dissolved in absolute alcohol (200 ml) and the solution was heated at reflux while sodium metal (2.4 g) was added in portions. It was maintained at reflux for a further 2 hr., when tlc indicated incomplete reaction. Further sodium metal (2.4 g) was added then, and again (2.4 g)after another 6 hr., the heating being continued for 12 hr. in tote. The ethanol was evaporated in vacuo to give an oil which was partitioned between ether and 2M hydrochloric acid. The aqueous layer was separated, basified with 2M sodium hydroxide solution and extracted with ether (2×150 ml). The ether layer was dried (magnesium sulphate) and evaporated in vacuo to give an oil (2.6 g). This was purified by column chromatography on silica gel and 3-phenyl-1,2,3,4-tetrahydroisoquinoline was eluted with dichloromethane/methanol characterised by its nmr spectrum.

Workup

  1. temperaturethe solution was heated
  2. additionwas added in portions
  3. temperatureIt was maintained
  4. temperatureat reflux for a further 2 hr
  5. customreaction
  6. wait, the heating being continued for 12 hr
  7. customThe ethanol was evaporated in vacuo
  8. customto give an oil which
  9. customwas partitioned between ether and 2M hydrochloric acid
  10. customThe aqueous layer was separated
  11. extractionextracted with ether (2×150 ml)
  12. dry with materialThe ether layer was dried (magnesium sulphate)
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-3a8c60f23e3c41bd9ca4d2568102cbd1
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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