Methanol → HCID 86614376, compound

HRID 1817795Notes

Reaction equation

HRID 1817795 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.CO.[S:22]([S:26]([O-:28])=[O:27])([O-:25])(=[O:24])=[O:23].[Na+:29].[Na+]>O>[S:22]([S:26]([O-:28])=[O:27])([O-:25])(=[O:24])=[O:23].[Na+:29].[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[O:17])=[CH:18][CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[Na+:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 656671Sodium PyrosulfiteHCID 104225464-{2-[Methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Product 1

HCID 86614376HCID 86614376, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzaldehyde (20 gms, 84% HPLC purity) was stirred with methanol (200 ml) and cooled to 15° C. A solution of sodium metabisulphite (22 gms, 0.115M) in water (40 ml) was added drop wise to the above solution over a time period of about 15 to 20 minutes, whilst maintaining the temperature below about 20° C. The reaction mixture was then cooled to 10° C. and stirred for about 2 hours. The resulting solid precipitate was then filtered and washed with methanol (25 ml) and water (25 ml). The solid was then dried in a vacuum oven at 40° C. to obtain the title compound (20 gms, 98% HPLC purity).

Workup

  1. temperaturewhilst maintaining the temperature below about 20° C
  2. temperatureThe reaction mixture was then cooled to 10° C.
  3. filtrationThe resulting solid precipitate was then filtered
  4. washwashed with methanol (25 ml) and water (25 ml)
  5. customThe solid was then dried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-c7dca6d9da764c77895c5bcc4733e54d
Source dataset
uspto-grants-2009_10
Patent number
US07598387B2

Reaction notes

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