Acetic Acid → Methyl((quinolin-3-yl)methyl)amine

HRID 1920994Notes

Reaction equation

HRID 1920994 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.CN.CO.CC(O)=O.[BH3-][C:22]#[N:23].[Na+]>CO>[CH3:22][NH:23][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 836413-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57454252Monomethylamine methanol

Product 1

HCID 16494781Methyl((quinolin-3-yl)methyl)amineYield 48.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-quinolinecarboxaldehyde (1.5 g, 10 mmole), 2.0 M CH3NH2/MeOH (10 mL, 20 mmole), glacial AcOH (0.6 mL, 10 mmole), and NaBH3CN (0.35 g, 11 mmole) in MeOH (20 mL) was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 5% NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel (10% MeOH/CH2Cl2) gave the title compound (0.83 g, 24%) as a slightly yellow viscous oil: MS (ES) m/e 173 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with 5% NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22c4c353c9914fb097a7c36cad2ff232
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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