Sodium cyanoborohydride → HCID 15678873, compound

HRID 258080Notes

Reaction equation

HRID 258080 reaction equation
[C:1]([BH3-])#[N:2].[Na+].Cl.CN.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH:13]2[CH2:22][CH:23]=O>CO>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH:13]2[CH2:22][CH2:23][NH:2][CH3:1]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 156788721,2,3,4-Tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinolineacetaldehyde

Product 1

HCID 15678873HCID 15678873, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (1.2 g) was added to a solution of 10.0 g of methylamine hydrochloride and 4.6 g of 1,2,3,4-tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinolineacetaldehyde in 142 ml of methanol. The solution was stirred at room temperature for 19 hours, quenched with 10% hydrochloric acid solution and extracted with ethyl acetate. The aqueous layer was basified with potassium hydroxide and the product extracted into ethyl acetate. The combined organic layers were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. Column chromatography on silica gel (elution with triethylamine-methanol-ethyl acetate) afforded 3,4-dihydro-6-methoxy-1-methyl-4-[2-(methylamino)ethyl]-2(1H)-quinolinone as a solid. To a solution of the amine in methanol was added ethereal hydrochloric acid to pH 1. The solvent was removed, and the residue recrystallized from isopropanol-diethyl ether to afford the hydrochloride salt, m.p. 175°-177° C.

Workup

  1. customquenched with 10% hydrochloric acid solution
  2. extractionextracted with ethyl acetate
  3. extractionthe product extracted into ethyl acetate
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-d6eacada28774ff990e6cbb5faebe9be
Source dataset
uspto-grants-1993_11
Patent number
US05264575

Reaction notes

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