2,6-Diaminopyridine → 5,7-Bis(pentafluoroethyl)-1,8-naphthyridin-2-amine

HRID 437388Notes

Reaction equation

HRID 437388 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[F:9][C:10]([F:27])([F:26])[C:11]([F:25])([F:24])[C:12](=O)[CH2:13][C:14](=O)[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17].[OH-].[NH4+]>P(=O)(O)(O)O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:4](=[N:8][C:14]([C:15]([F:20])([F:21])[C:16]([F:17])([F:18])[F:19])=[CH:13][C:12]=2[C:11]([F:25])([F:24])[C:10]([F:27])([F:26])[F:9])[N:3]=1

Participants

5

Reactant 3

HCID 88612,6-DiaminopyridineHCID 14923Ammonium HydroxideHCID 27696524H,4H-Decafluoroheptane-3,5-dione

Product 1

HCID 214283845,7-Bis(pentafluoroethyl)-1,8-naphthyridin-2-amine

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

A mixture of 2,6-diamino pyridine (5.2 g., 4.76 mmole), 1,1,1,2,2,6,6,7,7,7-decafluoroheptan-3,5-dione (14.5 g., 4.80 mmole) and 85% phosphoric acid (50 ml.) is stirred at 90°-95° C. for 6 hours. When cool, the reaction mixture is poured into ice-water and neutralized with ammonium hydroxide to pH 7. The solid is collected, washed with water, dried, and can be purified by recrystallization from benzene.

Workup

  1. temperatureWhen cool
  2. customThe solid is collected
  3. washwashed with water
  4. customdried
  5. customcan be purified by recrystallization from benzene

Sources & evidence

ORD record
ord-4750b8ae41cf404fa092dd547ec39d24
Source dataset
uspto-grants-1977_06
Patent number
US04031103

Reaction notes

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