Pyridine → 2-(4-Hydroxyphenyl)pyrimidine-5-carbonitrile

HRID 2198509Notes

Reaction equation

HRID 2198509 reaction equation
[CH2:1](N(CC)CC)C.Cl.[OH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[NH:15])=[CH:12][CH:11]=1.[N:19]1[CH:24]=[CH:23][CH:22]=CC=1>>[C:24]([C:23]1[CH:1]=[N:15][C:14]([C:13]2[CH:17]=[CH:18][C:10]([OH:9])=[CH:11][CH:12]=2)=[N:16][CH:22]=1)#[N:19]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 217124Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1)

Product 1

HCID 1356751332-(4-Hydroxyphenyl)pyrimidine-5-carbonitrile

Procedure

50 ml abs. triethylamine, 50 ml abs. pyridine, 17.3 g (0.1 mol) 4-hydroxybenzamidine-hydrochloride and 11 g (0.1 mol) α-cyano-β-dimethylamino-acroleine are heated upon stirring for 6 hours to 80° C. Dark brown colored reaction mixture is poured on ice/concentrated H2SO4 (500 g/50 ml), the precipitate is removed by suction, washed thoroughly with water and recrystallized from methanol/activated carbon. The yield is 12.8 g (65% of the theoretical value). m.p.: 160-262 (sublimed).

Workup

  1. additionDark brown colored reaction mixture is poured on ice/concentrated H2SO4 (500 g/50 ml)
  2. customthe precipitate is removed by suction
  3. washwashed thoroughly with water
  4. customrecrystallized from methanol/activated carbon

Sources & evidence

ORD record
ord-da070beb09244ff6a9b64ecf21807a84
Source dataset
uspto-grants-1982_11
Patent number
US04358393

Reaction notes

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