Acetic Acid → 5-Chloro-1,2,3,4-tetrahydroquinoline

HRID 1649418Notes

Reaction equation

HRID 1649418 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=O)[NH:7]2.[BH4-].[Na+].C(O)(=O)C>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][NH:7]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 190277365-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 114806665-Chloro-1,2,3,4-tetrahydroquinolineYield 91.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

42.5 g of 5-chloro-3,4-dihydrocarbostyril was suspended in 250 ml of dioxane and 44.3 g of NaBH4 was added to the suspension. Then 67 ml of acetic acid (d=1.05) was added dropwise to the mixture at room temperature. After heat-refluxing the resulting mixture for 2 hours the solvent was removed under reduced pressure. Water was added to the residue and insoluble materials were removed by filtration followed by washing with diethyl ether. The residue was extracted with diethyl ether, dried over anhydrous sodium sulfate and distilled under reduced pressure to obtain 36.0 g of 5-chloro-1,2,3,4-tetrahydroquinoline having a boiling point of 116° to 120° C./0.2 mmHg.

Workup

  1. temperatureAfter heat-refluxing the resulting mixture for 2 hours the solvent
  2. customwas removed under reduced pressure
  3. additionWater was added to the residue and insoluble materials
  4. customwere removed by filtration
  5. washby washing with diethyl ether
  6. extractionThe residue was extracted with diethyl ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-10951722a7e14f76ab94d25cfddc71cb
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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