3,4-Diaminopyridine → HCID 178488902, compound

HRID 1200230Notes

Reaction equation

HRID 1200230 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:9][O:10][C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=O.P(Cl)(Cl)([Cl:24])=O>>[ClH:24].[CH3:9][O:10][C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:12]=1[C:13]1[NH:8][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 59183,4-DiaminopyridineHCID 70522,4-Dimethoxybenzoic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 178488902HCID 178488902, compoundYield 57%

Procedure

A mixture of 3,4-diaminopyridine (10.90 g., 100 mmoles) and 2,4-dimethoxybenzoic acid (18.20 g., 100 mmoles) was added to 400 ml. of phosphorous oxychloride and the resulting mixture was heated to reflux for about 4 hours. After cooling, the excess phosphorous oxychloride was removed under reduced pressure and the residue was treated with 200 ml. of 1N hydrochloric acid. The resulting solution was neutralized with 50% aqueous sodium hydroxide and the precipitated product was collected by filtration. Flash chromatography over silica gel (methylene chloride/methanol, 15:1) and recrystallization from ethanol/water saturated with hydrogen chloride gave the title product (16.54 g., 57% yield) as light tan needles, m.p. about 231°-234° C.

Workup

  1. additionwas added to 400 ml
  2. temperatureto reflux for about 4 hours
  3. temperatureAfter cooling
  4. customthe excess phosphorous oxychloride was removed under reduced pressure
  5. additionthe residue was treated with 200 ml
  6. filtrationthe precipitated product was collected by filtration
  7. customFlash chromatography over silica gel (methylene chloride/methanol, 15:1) and recrystallization from ethanol/water saturated with hydrogen chloride

Sources & evidence

ORD record
ord-9ba9cfd5b7434ee28f32afbc975578ed
Source dataset
uspto-grants-1990_02
Patent number
US04904785

Reaction notes

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