Hydrochloric Acid → HCID 19697721, compound

HRID 2292118Notes

Reaction equation

HRID 2292118 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Cl>O>[C:1]1([CH:7]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2828493-phenylquinolineHCID 5360545Sodium

Product 1

HCID 19697721HCID 19697721, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-phenylquinoline (0.5 g) was dissolved in refluxing absolute alcohol (25 ml) and sodium metal (0.28 g) was added portionwise over 30 min. The reaction mixture was then refluxed for 3 hr. The cooled reaction mixture was diluted with water and acidified with conc. hydrochloric acid, the ethanol was removed in vacuo. The reaction mixture was basified with 10M sodium hydroxide solution and extracted with chloroform (2×100 ml). The chloroform extract was dried (magnesium sulphate), decolorised with activated charcoal and evaporated in vacuo to give 1,2,3,4-tetrahydro-3-phenylquinoline as a semi-solid which was crystallised from petroleum-ether (40°-60°), as an off-white solid, m.pt. 84°-86°, characterised by its nmr spectrum.

Workup

  1. additionwas added portionwise over 30 min
  2. temperatureThe reaction mixture was then refluxed for 3 hr
  3. customThe cooled reaction mixture
  4. customthe ethanol was removed in vacuo
  5. extractionextracted with chloroform (2×100 ml)
  6. extractionThe chloroform extract
  7. dry with materialwas dried (magnesium sulphate)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-0d4f7001188c446fbc618cbf733bb28e
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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