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

HRID 437387Notes

Reaction equation

HRID 437387 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[CH2:9]([C:16]([C:18]([F:21])([F:20])[F:19])=O)[C:10]([C:12]([F:15])([F:14])[F:13])=O.[OH-].[NH4+]>P(=O)(O)(O)O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:4](=[N:8][C:10]([C:12]([F:13])([F:14])[F:15])=[CH:9][C:16]=2[C:18]([F:19])([F:21])[F:20])[N:3]=1

Participants

5

Reactant 3

HCID 88612,6-DiaminopyridineHCID 14923Ammonium HydroxideHCID 73706Hexafluoroacetylacetone

Product 1

HCID 27830715,7-Bis(trifluoromethyl)-1,8-naphthyridin-2-amine

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

A mixture of 2,6-diaminopyridine (5.2 g., 47.6 mmole), 1,1,1,5,5,5-hexafluoroacetylacetone (10.0 g., 48.0 mmole) and 85% phosphoric acid (50 ml.) are stirred for six hours in an oil-bath at 90°-95° C. then left overnight at ambient temperature. The reaction mixture is poured into ice water and neutralized with ammonium hydroxide to pH 7, the solid collected, washed with water and dried to provide 9.0 g. (67%) of product, m.p. 198-204° C. Upon recrystallization from benzene, purified product separates in the form of pale yellow needles, m.p. 204°-206° C.

Workup

  1. waitthen left overnight at ambient temperature
  2. customthe solid collected
  3. washwashed with water
  4. customdried
  5. customto provide 9.0 g
  6. customUpon recrystallization from benzene
  7. custompurified product separates in the form of pale yellow needles, m.p. 204°-206° C.

Sources & evidence

ORD record
ord-52662a937ed8469c9a90b254e503e016
Source dataset
uspto-grants-1977_06
Patent number
US04031103

Reaction notes

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