Methanol → HCID 17763826, compound

HRID 1817793Notes

Reaction equation

HRID 1817793 reaction equation
[CH3:1][N:2]([CH:9](O)[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[H-].[Na+].C[OH:24]>CN(C=O)C>[CH3:1][N:2]([CH2:9][CH2:10][O:24][C:19]1[CH:20]=[CH:13][CH:14]=[CH:15][C:16]=1[CH:17]=[O:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydride3×HCID 680234-FluorobenzaldehydeHCID 22574377HCID 22574377, compound

Product 1

HCID 17763826HCID 17763826, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

2-(N-methyl-N-(2-pyridyl)amino ethanol (50 gms, 0.32M) and 4-fluoro benzaldehyde (68 gms, 0.547M) were dissolved in DMF (500 ml) and sodium hydride (2 gms) was added. The reaction mass was stirred for 15 minutes and the temperature was maintained below 35° C. Sodium hydride (4 gms) was added again and the reaction mass stirred for 15 minutes. Subsequently 8 and 10 gms of sodium hydride were sequentially added at 15 minute intervals. The reaction was monitored by HPLC. After completion of reaction, the reaction mass was cooled to 5° C., and methanol (30 ml) was added slowly. The reaction mass was then quenched into water (approx 21 trs) and extracted with ethyl acetate (4×500 ml). The combined organic layers were washed with water (6×500 ml). The organic layer was dried over sodium sulphate and concentrated to obtain the title compound as an oil (105 gms, 84% HPLC purity).

Workup

  1. temperaturethe temperature was maintained below 35° C
  2. stirringthe reaction mass stirred for 15 minutes
  3. customAfter completion of reaction
  4. customThe reaction mass was then quenched into water (approx 21 trs)
  5. extractionextracted with ethyl acetate (4×500 ml)
  6. washThe combined organic layers were washed with water (6×500 ml)
  7. dry with materialThe organic layer was dried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e461dd9bcab14a3798724456dcd045bc
Source dataset
uspto-grants-2009_10
Patent number
US07598387B2

Reaction notes

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