Acetonitrile → HCID 117888949, compound

HRID 632512Notes

Reaction equation

HRID 632512 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(#N)C.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CCOC(C)=O.O>[O:34]1[CH2:35][CH2:36][N:31]([CH2:30][CH2:29][O:1][C:2]2[CH:9]=[C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:32][CH2:33]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86713214HCID 86713214, compound

Product 1

HCID 117888949HCID 117888949, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To 1.0 g of 2-hydroxy-4-(2-pyridylmethoxy)benzaldehyde were successively added 30 mL of acetonitrile, 4.26 g of cesium carbonate and 0.85 g of 4-(2-chloroethyl)morpholine hydrochloride. The mixture was stirred at 90° C. for 2 hours. To the reaction mixture, 50 mL of water and 150 mL of AcOEt were added, and the organic layer was separated. The obtained organic layer was dried over Na2SO4 and concentrated to give 1.56 g of the title compound in quantitative yield.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe obtained organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0ab8a4bf37dc4d85b2ebb9c99508df75
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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