Sodium hydride → HCID 86711539, compound

HRID 512497Notes

Reaction equation

HRID 512497 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)#[N:14]>CN(C=O)C.O>[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:5]2[CH:4]=[CH:3][C:2](=[O:1])[C:7]([C:8]([OH:10])=[O:9])=[CH:6]2)=[CH:17][CH:16]=1)#[N:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 178524755HCID 178524755, compound

Product 1

HCID 86711539HCID 86711539, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-hydroxynicotinic acid (2.00 g, 14.4 mmol) in DMF (30 mL) is added sodium hydride (0.62 g, 55% dispersion in mineral oil, 14.2 mmol). After stirring for 10 min at room temperature, 4-cyanobenzyl bromide (2.88 g, 14.7 mmol) is added. After stirring for 2 h at room temperature, DMF (15 mL) is added and the reaction mixture is diluted with water. The formed precipitate is filtered off and dried. Yield: 2.57 g (56% of theory); ESI mass spectrum: [M+H]+=255; Retention time HPLC: 0.68 min (Z002—002).

Workup

  1. stirringAfter stirring for 2 h at room temperature
  2. filtrationThe formed precipitate is filtered off
  3. customdried
  4. custom0.68 min (Z002—002)

Sources & evidence

ORD record
ord-f8ea09e6f55749a7a65ed37da439ba26
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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