3,4-Diaminopyridine → HCID 178486753, compound

HRID 462427Notes

Reaction equation

HRID 462427 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[C:12]([C:23](O)=O)=[CH:13][C:14]2[C:19]([CH:20]=1)=[C:18]([O:21][CH3:22])[CH:17]=[CH:16][CH:15]=2.P(Cl)(Cl)(Cl)=O>>[CH3:9][O:10][C:11]1[C:12]([C:23]2[NH:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=2)=[CH:13][C:14]2[C:19]([CH:20]=1)=[C:18]([O:21][CH3:22])[CH:17]=[CH:16][CH:15]=2

Participants

4

Reactant 3

HCID 59183,4-DiaminopyridineHCID 24813Phosphorus oxychlorideHCID 12535213,5-dimethoxy-2-naphthoic acid

Product 1

HCID 178486753HCID 178486753, compound

Procedure

A solution of 4.1 g. of 3,4-diaminopyridine and 8.7 g. of 3,5-dimethoxy-2-naphthoic acid in 250 ml. of phosphorous oxychloride was heated at reflux for 18 hours. The reaction was cooled and evaporated in vacuo. The solid was dissolved in 2N hydrochloric acid, cooled, and adjusted to pH 8. The resulting solid was recovered by filtration and chrom;atographed over silica gel to afford 4.4 g. of the desired title compound, m.p. 178°-180° C.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. customevaporated in vacuo
  4. dissolutionThe solid was dissolved in 2N hydrochloric acid
  5. temperaturecooled
  6. filtrationThe resulting solid was recovered by filtration and chrom
  7. customto afford 4.4 g

Sources & evidence

ORD record
ord-9b392bf288aa4c9789f12b29e19566ec
Source dataset
uspto-grants-1985_05
Patent number
US04515796

Reaction notes

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