3,4-Diaminopyridine → HCID 178488903, compound

HRID 746220Notes

Reaction equation

HRID 746220 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[Cl:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:15]=1[C:16](O)=O>P(Cl)(Cl)(Cl)=O>[CH3:24][O:23][C:21]1[CH:20]=[CH:19][C:15]([C:16]2[NH:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=2)=[C:14]([O:13][CH2:12][CH2:11][CH2:10][Cl:9])[CH:22]=1

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 233106382-(3-Chloropropoxy)-4-methoxybenzoic acid

Product 1

HCID 178488903HCID 178488903, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 3,4-diaminopyridine and 2-(3-chloropropoxy)-4-methoxybenzoic acid in phosphorus oxychloride was stirred at reflux for 4 hours. The excess phosphorus oxychloride was then removed in vacuo and the residue carefully treated with water before basifying with dilute ammonia hydroxide and extracting with chloroform. The crude product was then dissolved in ethyl acetate, decolourised with charcoal and triturated with ethereal HCl to give the title compound m.p. 174°-176° C.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe excess phosphorus oxychloride was then removed in vacuo
  3. additionthe residue carefully treated with water
  4. extractionextracting with chloroform
  5. dissolutionThe crude product was then dissolved in ethyl acetate
  6. customtriturated with ethereal HCl

Sources & evidence

ORD record
ord-41049bbb29e240de815c6c556156022a
Source dataset
uspto-grants-1986_07
Patent number
US04603139

Reaction notes

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