Sodium Hydroxide → HCID 10445611, compound

HRID 2257067Notes

Reaction equation

HRID 2257067 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][NH:9][C:10](=O)OC)[CH:2]=1.[OH-].[Na+].N[C:17]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:18]=1C=O>OS(O)(=O)=O>[CH3:26][O:25][C:23]1[CH:24]=[C:17]2[C:10](=[CH:21][C:22]=1[O:27][CH3:28])[N:9]=[CH:8][C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[CH:18]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 108885432-Amino-4,5-dimethoxybenzaldehydeHCID 54022183methyl N-2-(pyrid-3-yl)vinylcarbamate

Product 1

HCID 10445611HCID 10445611, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
22 °C

Procedure

A solution of 600 mg (3.37 mmol) of methyl N-2-(pyrid-3-yl)vinylcarbamate in 10 mL of 6N H2SO4 is refluxed for 10 minutes, cooled to 0° C. and basified to pH 11 with 50% NaOH. A solution of 400 mg (2.03 mmol) of 2-amino-4,5-dimethoxybenzaldehyde is immediately added and the mixture refluxed for 2.5 hours, cooled to 22° C. and partitioned between ether (150 mL) and water (100 mL). The aqueous layer is back extracted with chloroform and the combined organics are dried (MgSO4) and evaporated to obtain an oil which is recrystallized from hexane/ethyl acetate twice to give 3-(6,7-dimethoxyquinolin-3-yl)pyridine (m.p. 131°-132° C.).

Workup

  1. temperaturethe mixture refluxed for 2.5 hours
  2. custompartitioned between ether (150 mL) and water (100 mL)
  3. extractionThe aqueous layer is back extracted with chloroform
  4. dry with materialthe combined organics are dried (MgSO4)
  5. customevaporated
  6. customto obtain an oil which
  7. customis recrystallized from hexane/ethyl acetate twice

Sources & evidence

ORD record
ord-c2c395f3f2bf440eb5a04740b14b3c8e
Source dataset
uspto-grants-1997_08
Patent number
US05656643

Reaction notes

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