Water → 5-((Diphenylmethylene)amino)nicotinaldehyde

HRID 82183Notes

Reaction equation

HRID 82183 reaction equation
[C:1]1([C:7](=[N:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([CH:26]=2)[C:20](N(OC)C)=[O:21])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]C(C)C)(C)C.O.C(OCC)(=O)C>C1COCC1>[C:1]1([C:7](=[N:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([CH:26]=2)[CH:20]=[O:21])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21896610Diisopropylaluminium hydrideHCID 866720805-((Diphenylmethylene)amino)-N-methoxy-N-methylnicotinamide

Product 1

HCID 866721015-((Diphenylmethylene)amino)nicotinaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a stirred solution of 5-[(diphenylmethylene)amino]-N-methoxy-N-methylnicotinamide (Preparation 23, 7.50 g, 0.021 mol) in THF (150 mL) at −70° C. was added diisopropylaluminium hydride (42 mL, 0.042 mol, 1.0 M in THF) and the resulting mixture stirred at −70° C. for 2 hours. Water (20 mL) and ethyl acetate (100 mL) were added. The organic phase was separated, concentrated under reduced pressure and purified by silica gel column chromatography eluting with EtOAc: petroleum ether 1:10 to afford the title compound as a brown solid in 65% yield, 4 g.

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated under reduced pressure
  3. custompurified by silica gel column chromatography
  4. washeluting with EtOAc: petroleum ether 1:10

Sources & evidence

ORD record
ord-fd2efcc8663b4a3baa881ce9f54d9982
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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