Isopropylamine → HCID 59569672, compound

HRID 2071090Notes

Reaction equation

HRID 2071090 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:18]([NH2:21])([CH3:20])[CH3:19]>CN(C=O)C.CCOCC.[Cu](I)I>[CH:18]([NH:21][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8])([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 6363IsopropylamineHCID 62657Potassium Phosphate, TribasicHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 59569672HCID 59569672, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 5-bromonicotinaldehyde (1.5 gm, 8.06 mmol) in DMF (5 ml), N,N-diethylsalicylidiamide (311 mg, 1.61 mmol), copper iodide (77 mg, 0.403 mmol), potassium phosphate (3.42 gm, 16.12 mmol) and isopropylamine (715 mg, 1.21 mmol) were added and the reaction mixture was heated overnight at 90° C. Then reaction mixture was diluted with ether and filtered. Ether layer was washed with water, brine and dried. Crude residue was column chromatographed (40% ethylacetate/60% Hexanes) to yield 5-(isopropylamino)nicotinaldehyde.

Workup

  1. customThen reaction mixture
  2. filtrationfiltered
  3. washEther layer was washed with water, brine
  4. customdried
  5. customchromatographed (40% ethylacetate/60% Hexanes)

Sources & evidence

ORD record
ord-777c88df6c5547edbf78a00c109b0025
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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