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

HRID 1657820Notes

Reaction equation

HRID 1657820 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-15ec308737654b12a1bafc1ebe8134f2
Source dataset
uspto-grants-1976_06
Patent number
US03962262

Reaction notes

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