Water → 5,6,7,8-Tetrahydro-7-(methylamino)quinoline

HRID 1461292Notes

Reaction equation

HRID 1461292 reaction equation
[Cl-].[CH3:2][NH3+:3].[N:4]1[C:13]2[CH:12]=[CH:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.O.[OH-].[Na+]>CO.[Cl-].[Na+].O.C(OCC)(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][NH:3][CH:11]1[CH2:12][C:13]2[N:4]=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:9][CH2:10]1

Participants

9

Reactant 4

HCID 962WaterHCID 11637Methanamine, hydrochloride (1:1)HCID 14798Sodium HydroxideHCID 123183175,6-Dihydroquinoline

Product 1

HCID 148359215,6,7,8-Tetrahydro-7-(methylamino)quinolineYield 83.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolventHCID 21584019Toluene ethylacetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methylammonium chloride (1.35 g, 20 mmol) in methanol (2 ml) was added to 5,6-dihydroquinoline (1.31 g, 10 mmol) in methanol (2 ml) and the solution was heated under reflux for 21h, poured onto a mixture of water (25 ml) and brine (25 ml), and basified with 10N-NaOH (25 ml). The mixture was extracted with chloroform (3×25 ml), and the extracts were dried (Na2SO4) and concentrated in vacuo to give an orange oil. Chromatography [alumina; ethyl acetate-toluene (1:4)→ethyl acetate] gave the product (1.35 g) as an oil which was identical to the compound isolated in Example 2.

Workup

  1. temperaturethe solution was heated
  2. extractionThe mixture was extracted with chloroform (3×25 ml)
  3. dry with materialthe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil

Sources & evidence

ORD record
ord-8fed0ceb97524b93b7d35b54634c528a
Source dataset
uspto-grants-1991_12
Patent number
US05075303

Reaction notes

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