Sodium Hydroxide → α,α-Diphenyl-2-pyridinebutanamide

HRID 974969Notes

Reaction equation

HRID 974969 reaction equation
[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)#[N:2].[OH-:24].[Na+]>S(=O)(=O)(O)O>[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:24])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19970194HCID 19970194, compound

Product 1

HCID 19970203α,α-Diphenyl-2-pyridinebutanamideYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-(3-cyano-3,3-diphenylpropyl)pyridine (5.0 g, 16.8 mmol) (prepared as described in U.S. Pat. No. 2,649,455) in 90% sulphuric acid (10 ml) was heated at 95° C. for 3.5 hours, allowed to cool to room temperature, poured onto ice and basified with 5M aqueous sodium hydroxide solution. The resulting precipitate was collected, washed with water, dried and recrystallised from 2-propanol to give the title compound (4.5 g, 85%) as colourless crystals, m.p. 145°-146° C.

Workup

  1. additionpoured onto ice
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customdried
  5. customrecrystallised from 2-propanol

Sources & evidence

ORD record
ord-add5fd3e08774bb281ffa28b448bc4e3
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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