Diethyl Ether → 5-Morpholinonicotinaldehyde

HRID 1962757Notes

Reaction equation

HRID 1962757 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.C[CH2:15][O:16]CC.C([Li])CCC.CN(C=O)C>CCCCCC>[N:8]1([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([CH:3]=2)[CH:15]=[O:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 467396144-(5-Bromopyridin-3-yl)morpholineHCID 178418339Butyllithium

Product 1

HCID 574778965-MorpholinonicotinaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 4-(5-bromopyridin-3-yl)morpholine (100 mg, 0.0004 mol) in ether (2 mL, 0.02 mol) cooled at −78° C. was treated with 2.5 M n-butyllithium in hexane (0.2 mL) and was stirred for 1 h. To this mixture was added DMF (0.5 mL, 0.006 mol) dropwise. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give 5-morpholin-4-ylnicotinaldehyde (70 mg, 90%) as a crude product. 1H NMR (400 MHz, CDCl3): 10.1 (s, 1H), 8.0 (s, 2H), 7.6 (s, 1H), 3.8 (m, 4H), 3.2 (m, 4H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e65867acb6d240d2b5448de97350d9bd
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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