Water → 5-Benzyloxy-2-chloronicotinonitrile

HRID 1758498Notes

Reaction equation

HRID 1758498 reaction equation
[Cl:1][C:2]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[CH2:13]([O:10][C:7]1[CH:8]=[N:9][C:2]([Cl:1])=[C:3]([CH:6]=1)[C:4]#[N:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 128520202-Chloro-5-hydroxypyridine-3-carbonitrile

Product 1

HCID 128520215-Benzyloxy-2-chloronicotinonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a flame dried flask under N2 was placed 2-chloro-5-hydroxynicotinonitrile (2.0 g, 0.012 mol), DMF (60 mL), NaH (50% oil dispersion, 0.75 g, 0.013 mol) and the mixture cooled to 0°-4° C. A solution of benzyl bromide (1.5 mL, 0.013 mol) in DMF (2 mL) was then added and the solution allowed to stir at room temperature overnight. The mixture was poured into H2O and extracted with Et2O (3X). The organic layer was concentrated to yield 2.0 g (100%) of 5-benzyloxy-2-chloronicotinonitrile. An analytical sample of 5-benzyloxy-3-chloronicotinonitrile was prepared by trituration with C6H14, mp 114°-15° C.; 1H NMR (CDCl3) δ 5.2 (2H, s) 7.4 (5H, s), 7.5 (1H, d, J=3) and 8.35 (1H, d, J=3); IR (nujol) 2220 cm-1 ; MS m/e M+ 244.

Workup

  1. customTo a flame dried flask under N2
  2. temperaturethe mixture cooled to 0°-4° C
  3. extractionextracted with Et2O (3X)
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-d3201fb215734080a85ba666bdc1f46a
Source dataset
uspto-grants-1983_02
Patent number
US04374140

Reaction notes

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