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

HRID 649204Notes

Reaction equation

HRID 649204 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19].Cl>CCOCC>[C:18]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 3478501-Acetyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1,2,3,4-Tetrahydroquinoline (5 g, 0.038 mol) and triethylamine (4.55 g, 0.045 mol) were dissolved in 55 ml ether. Acetyl chloride (3.24 g, 0.041 mol) was added and the mixture stirred for 30 minutes, and poured into a mixture of 100 ml 1M HCl and 50 ml ether. The organic layer was separated, washed 1×100 ml 1M HCl and then 2×100 ml 5% NaHCO3, dried (K2CO3) and stripped to yield title product as an oil, 5.13 g.

Workup

  1. customThe organic layer was separated
  2. washwashed 1×100 ml 1M HCl
  3. dry with material2×100 ml 5% NaHCO3, dried (K2CO3)

Sources & evidence

ORD record
ord-b27cc9de5c3548c18cd968541e2beb27
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Reaction notes

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