Water → 8-methoxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde

HRID 85265Notes

Reaction equation

HRID 85265 reaction equation
[OH:1][C:2]1[C:13]2=[C:14]3[N:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8][CH2:7][CH2:6][C:5]3=[CH:4][C:3]=1[CH:15]=[O:16].CI.[C:19](=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[CH3:19][O:1][C:2]1[C:13]2=[C:14]3[N:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8][CH2:7][CH2:6][C:5]3=[CH:4][C:3]=1[CH:15]=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1130999-Formyl-8-julolidinol

Product 1

HCID 8202598-methoxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

In 20 ml of 1-methyl-2-pyrrolidone was dissolved 2.5 g (11.5 mmol) of 8-hydroxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboaldehyde, and 4.1 g (28.9 mmol) of methyl iodide and 4.8 g (34.7 mmol) of anhydrous potassium carbonate were added thereto. The mixture was stirred at 50° C. for 4 hours. After the reaction mixture was added to water, extraction with ethyl acetate, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 2.63 g of a yellow crystal (yield: 99.0%).

Workup

  1. additionwere added
  2. dry with materialdrying over anhydrous sodium sulfate, and concentration
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aa1948e76e104e5483cb42154963a52d
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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