Hydrochloric Acid → Quinolinepropionic acid, 1,2,3,4-tetrahydro-

HRID 446039

Reaction equation

HRID 446039 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:11]([O:15]C)(=[O:14])[CH:12]=[CH2:13].[Li+].[OH-].Cl>C(O)(=O)C.CO>[N:1]1([CH2:13][CH2:12][C:11]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 7294Methyl AcrylateHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 98707Quinolinepropionic acid, 1,2,3,4-tetrahydro-Yield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A mixture of 1,2,3,4-tetrahydroquinoline (3.0 g, 22.5 mmol) and methyl acrylate (3.9 g, 45.0 mmol) in acetic acid (15 mL) was refluxed for 16 hours. Upon cooling, volatiles were removed in the rotary evaporator and the residue obtained was co-evaporated with methanol (3×20 mL) and then dissolved in methanol (15 mL). To this mixture an aqueous solution of LiOH (1.9 g, 45 mmol) was added and it was stirred at room temperature for 2 hours. Reaction mixture was acidified with conc. HCl to pH ˜3 and extracted with ethyl acetate. The organic layer was washed twice with water and brine, dried over MgSO4 and evaporated to dryness to yield 2.91 g of Compound 7 as a dark brown viscous liquid. This product was used without any further purification. The structure of Compound 7 is given below:

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureUpon cooling
  3. customvolatiles were removed in the rotary evaporator
  4. customthe residue obtained
  5. customReaction mixture
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed twice with water and brine
  8. dry with materialdried over MgSO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-6a1fab905f824568b9f23e84d7c8db81
Source dataset
uspto-grants-2013_07
Patent number
US08476443B2

Linked notes

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