Sodium Hydroxide → HCID 59287378, compound

HRID 1927224Notes

Reaction equation

HRID 1927224 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 59287375HCID 59287375, compound

Product 1

HCID 59287378HCID 59287378, compoundYield 49.4%

Conditions

Temperature
100 °C

Procedure

2-Amino-6-methoxymethyl-nicotinamide (90 mg) described in Manufacturing Example 6-1 and phosphorus oxychloride (3.0 g) were stirred for 0.5 hour at 100° C. The reaction solution was added to 0° C. dilute aqueous sodium hydroxide and then extracted with ethyl acetate. The organic layer was concentrated and the residue was purified with silica gel chromatography (ethyl acetate) to obtain the titled compound (40 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified with silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4c98cf5e36cf44948fe0624a7d1bf5d2
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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