Phosphoric Acid → HCID 22253352, compound

HRID 1612382Notes

Reaction equation

HRID 1612382 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[CH2:24][C:25]#N)[CH2:4][CH3:5])[CH3:2].P(=O)(O)(O)[OH:28].[OH-].[Na+]>O>[CH2:1]([CH:3]([N:6]1[C:7]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:8]=2[CH2:24][C:25]1=[O:28])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 22596067HCID 22596067, compound

Product 1

HCID 22253352HCID 22253352, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetonitrile (800 mg, 2.27 mmol), 6 ml of 85% phosphoric acid and 2 ml of water was heated at reflux for 2 hours and cooled to room temperature. The reaction mixture was neutralized with 2N NaOH and extracted twice with chloroform. The chloroform layer was dried and concentrated to give a yellow solid. The solid was purified through silica gel column chromatography using hexane to 6% ethyl acetate in hexane as eluent to give 730 mg (92.2%) of a white solid. 1H NMR (CDCl3) δ 6.87(s,2H), 6.5(s,1H), 4.1(m,1H), 3.12(s,2H), 2.38(s,3H), 2.30(s,3H), 2.10(s,3H), 1.7–2.0(m,4H), 0.8(t,6H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted twice with chloroform
  4. dry with materialThe chloroform layer was dried
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customThe solid was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-90e4c187ea754193b9decfa86417e038
Source dataset
uspto-grants-2006_01
Patent number
US06992188B1

Reaction notes

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