3,4-Diaminopyridine → HCID 178488901, compound

HRID 746218Notes

Reaction equation

HRID 746218 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5](O)=O.[NH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH2:21]>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]1[NH:21][C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 70522,4-Dimethoxybenzoic acid

Product 1

HCID 178488901HCID 178488901, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

A mixture of 2,4 dimethoxybenzoic acid (2.5 g) and 3,4-diaminopyridine (1.5 g) was ground to a fine powder and added portionwise to phosphorus oxychloride (50 ml) with stirring. The mixture was stirred and heated under reflux for 2.5 hours before excess phosphorus oxychloride was removed in vacuo. The residue was cooled, water (20 ml) added and the pH adjusted to 7 with ammonium hydroxide to yield a pale yellow solid which was collected, washed with water and dried. The solid was recrystallised twice from aqueous ethanol to yield a cream coloured crystalline solid m.p. 195°-198°.

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated
  3. customwas removed in vacuo
  4. temperatureThe residue was cooled
  5. additionwater (20 ml) added
  6. customto yield a pale yellow solid which
  7. customwas collected
  8. washwashed with water
  9. customdried
  10. customThe solid was recrystallised twice from aqueous ethanol
  11. customto yield a cream

Sources & evidence

ORD record
ord-e9c5bbaa894449bbbd49705cc72ce31f
Source dataset
uspto-grants-1986_07
Patent number
US04603139

Reaction notes

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