Ethanol → HCID 58808779, compound

HRID 1921322Notes

Reaction equation

HRID 1921322 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:17]=[CH:18][C:19]([CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[C:20]([CH:23]=2)[C:21]#[N:22])=[CH:11][C:10]=1[CH2:31][CH3:32])C1C=CC=CC=1.C(O)C>[Pd].CCOCC>[CH2:31]([C:10]1[C:9](=[O:8])[NH:14][C:13]([CH3:15])=[C:12]([C:16]2[CH:17]=[CH:18][C:19]([CH2:24][N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[C:20]([CH:23]=2)[C:21]#[N:22])[CH:11]=1)[CH3:32]

Participants

5

Reactant 2

HCID 702EthanolHCID 67492341HCID 67492341, compound

Product 1

HCID 58808779HCID 58808779, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-(6-benzyloxy-5-ethyl-2-methylpyridin-3-yl)-2-(morpholin-4-yl)methylbenzonitrile (460 mg, 1.08 mmol), 5% palladium on charcoal (30 mg) and ethanol (15 mL) is stirred under an atmosphere of hydrogen. After 2.5 hr, the catalyst is separated by filtration through a pad of Hi-Flo. The filtrate is concentrated and the residue is stirred with ethereal hydrochloric acid. The solvent is removed to give a foam that is dissolved in ether and the solvent removed. This procedure is repeated twice more to afford 5-(5-ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(morpholin-4-yl)methylbenzonitrile (280 mg, 77%) as a pale yellow solid. LC/MS: MS m/e=338 (M+H); RT 0.38 min.

Workup

  1. customthe catalyst is separated by filtration through a pad of Hi-Flo
  2. concentrationThe filtrate is concentrated
  3. stirringthe residue is stirred with ethereal hydrochloric acid
  4. customThe solvent is removed
  5. customto give a foam that
  6. customthe solvent removed

Sources & evidence

ORD record
ord-8f7704ea5d4940388e5f4fbd092623fb
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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