Water → 4-Methyl-1,2-dihydroquinoline

HRID 2267124Notes

Reaction equation

HRID 2267124 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.B.C1COCC1.[H-].[H-].COCCO[Al+]OCCOC.[Na+].O>C1COCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:5][C:4]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][CH2:2][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 102854-MethylquinolineHCID 2723981Borane;tetrahydrofuranHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 128071714-Methyl-1,2-dihydroquinolineYield 43.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of lepidine (10.0 g) in THF was cooled down to −78° C., after which a solution of BH3.THF in THF (1 M, 70 ml) was added. After 2 h, a solution of sodium bis(2-methoxy-ethoxy)aluminum dihydride in toluene (3.5 M, 40 ml) was added and the reaction mixture was stirred for an additional 2 h. Water was added and the mixture diluted with ethyl acetate. The organic layer was separated, dried (MgSO4) and partially concentrated in vacuo causing crystallization of the title compound. The crystals were collected by filtration to yield 3.5 g after drying in vacuo. The remaining mother liquor was concentrated in vacuo and the residue was purified by chromatography on silicagel using heptane/ethyl acetate=0/1=>1/0 ( (v/v) as the eluent to give an additional 4.4 g of the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. concentrationpartially concentrated in vacuo
  4. customcrystallization of the title compound
  5. filtrationThe crystals were collected by filtration
  6. customto yield 3.5 g
  7. customafter drying in vacuo
  8. concentrationThe remaining mother liquor was concentrated in vacuo
  9. customthe residue was purified by chromatography on silicagel

Sources & evidence

ORD record
ord-a9329bdd205442ca81977d88e023dcc6
Source dataset
uspto-grants-2010_12
Patent number
US07858794B2

Reaction notes

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