Hydrochloric Acid → 2-Phenyl-1,2,3,4-tetrahydroquinoline

HRID 2292117Notes

Reaction equation

HRID 2292117 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Cl>O>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 715452-PhenylquinolineHCID 5360545Sodium

Product 1

HCID 107529152-Phenyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Phenylquinoline (65 g) was dissolved in absolute alcohol (200 ml) and heated to reflux when sodium metal (25 g) was added in portions over 1 hr. The resulting mixture was maintained at reflux for a further 3 hr. The mixture was diluted with water (300 ml) and acidified with conc. hydrochloric acid. The alcohol was removed in vacuo and the residue made basic with 10M sodium hydroxide solution. The resulting solution was extracted with ether (4×150 ml) and the ether layer was dried (magnesium sulphate) and evaporated in vacuo to give an oil which was distilled twice to give the product, 1,2,3,4-tetrahydro-2-phenylquinoline (b.pt. 114°/0.1 mm Hg). This was characterised by its nmr spectrum.

Workup

  1. temperatureheated
  2. additionwas added in portions over 1 hr
  3. temperatureThe resulting mixture was maintained
  4. temperatureat reflux for a further 3 hr
  5. customThe alcohol was removed in vacuo
  6. extractionThe resulting solution was extracted with ether (4×150 ml)
  7. dry with materialthe ether layer was dried (magnesium sulphate)
  8. customevaporated in vacuo
  9. customto give an oil which
  10. distillationwas distilled twice

Sources & evidence

ORD record
ord-3a38e7a0aac74c86b363628340687700
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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