2-Methoxyethanol → 2-Chloro-5-(2-methoxyethoxy)nicotinonitrile

HRID 219284Notes

Reaction equation

HRID 219284 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[N:28]=[CH:27][C:26]([OH:29])=[CH:25][C:22]=1[C:23]#[N:24].[CH3:30][O:31][CH2:32][CH2:33]O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:20][C:21]1[N:28]=[CH:27][C:26]([O:29][CH2:33][CH2:32][O:31][CH3:30])=[CH:25][C:22]=1[C:23]#[N:24]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 128520202-Chloro-5-hydroxypyridine-3-carbonitrile

Product 1

HCID 580155242-Chloro-5-(2-methoxyethoxy)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round bottom flask under N2 were dissolved triphenylphosphine (19 g, 73 mmol), 2-chloro-5-hydroxynicotinonitrile (7.5 g, 49 mmol), and 2-methoxyethanol (5.7 ml, 73 mmol) in THF (130 mL) followed by a slow addition of DEAD (27 ml, 68 mmol), and then stirred at room temperature. After 2 h the reaction showed full conversion to the desired compound. The crude mixture was purified by MPLC eluting with 100% DCM to 90% DCM: 10% MeOH to afford 2-chloro-5-(2-methoxyethoxy)nicotinonitrile (6.46 g, 63% yield) as a tan solid.

Sources & evidence

ORD record
ord-03e6a56cac024740a2b7a4ad76327f92
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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