Hydrochloric Acid → HCID 86716185, compound

HRID 512161Notes

Reaction equation

HRID 512161 reaction equation
[CH:1]1([CH2:4][CH:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]([O:16]CC)=[CH2:15])=[CH:12][CH:13]=2)[C:6]#[N:7])[CH2:3][CH2:2]1.Cl>C1COCC1>[C:14]([C:11]1[N:10]=[CH:9][C:8]([CH:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6]#[N:7])=[CH:13][CH:12]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86716183HCID 86716183, compound

Product 1

HCID 86716185HCID 86716185, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-cyclopropyl-2-(6-(1-ethoxyvinyl)pyridin-3-yl)propanenitrile (2 g, crude) in THF (10 mL) was added 4N HCl (10 mL) and stirred at room temperature for 2 h. The reaction mixture was adjusted pH to 6-7 by 4M aq.NaOH and extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel (EtOAc: Petroleum ether=1:10) to give 2-(6-acetylpyridin-3-yl)-3-cyclopropylpropanenitrile (600 mg, yield: 60%) 1H NMR (CDCl3 varian 400): δ8.58-8.51 (m, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.75 (dd, J=8.0 Hz, 2.4 Hz, 1H), 3.92-3.85 (m, 1H), 2.61 (s, 3H), 1.88-1.79 (m, 1H), 1.71-1.65 (m, 1H), 0.75-0.67 (m, 1H), 0.49-0.45 (m, 2H), 0.10-0.03 (m, 2H).

Workup

  1. extractionNaOH and extracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography on silica gel (EtOAc: Petroleum ether=1:10)

Sources & evidence

ORD record
ord-e48d73651d3945d68cc39df7a8f61c8b
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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