Formic Acid → HCID 10376640, compound

HRID 2164766Notes

Reaction equation

HRID 2164766 reaction equation
C(O)=O.C=O.NC1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH3:18])=[C:12]([O:19][CH3:20])[CH:11]=2.[OH-].[Na+].[CH3:23][N:24]([CH3:27])[CH:25]=O>O>[CH3:23][N:24]([CH3:27])[C:25]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH3:18])=[C:12]([O:19][CH3:20])[CH:11]=2

Participants

7

Reactant 5

HCID 284Formic AcidHCID 712FormaldehydeHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 103305386,7-Dimethoxyquinolin-3-amine

Product 1

HCID 10376640HCID 10376640, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 113.5 g (2.45 mole) of 99% formic acid and 200 ml of formaldehyde (36.5% w/v) is added, under stirring and by cooling at 15°-20° C., to a solution of 100 g (0.49 mole) of 3-amino-6,7-dimethoxyquinoline (prepared according to J. Med. Chem., 22, 1005, 1979) in 400 ml of N,N-dimethylformamide. The thus obtained mixture is refluxed for 6 hours, then water is added, the pH is adjusted to 10 with 40% NaOH and the mixture is extracted with ethyl acetate.

Workup

  1. additionis added
  2. temperatureThe thus obtained mixture is refluxed for 6 hours
  3. extractionthe mixture is extracted with ethyl acetate

Sources & evidence

ORD record
ord-2b61512cdc494c3abff44204b1ee44fe
Source dataset
uspto-grants-1985_03
Patent number
US04507307

Reaction notes

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