5-Methyl-7-(1,1,2,2,2-pentafluoroethyl)-1,8-naphthyridin-2-amine → HCID 21428391, compound

HRID 437389Notes

Reaction equation

HRID 437389 reaction equation
N[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:7][C:8]=2[CH3:12])[N:3]=1.N([O-])=[O:21].[Na+]>FC(F)(F)C(O)=O>[CH3:12][C:8]1[CH:7]=[C:6]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2](=[O:21])[NH:3]2

Participants

4

Reactant 2

HCID 214283925-Methyl-7-(1,1,2,2,2-pentafluoroethyl)-1,8-naphthyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 21428391HCID 21428391, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Amino-5-methyl-7-pentafluoroethyl-1,8-naphthyridine (5.54 g., 20 mmole) is dissolved in trifluoroacetic acid (40 ml.) and to the stirred solution cooled to -5° to 0° C. is added finely powdered sodium nitrite (3.0 g., 43.5 mmole) in small portions. Stirring of the mixture is continued at room temperature for one hour, after which it is poured into ice-water (ca. 500 ml.). The product precipitates and is collected, washed and dried at 60° C. in air. It can be purified by recrystallization from diisopropyl ether.

Workup

  1. temperaturecooled to -5° to 0° C.
  2. customThe product precipitates
  3. customis collected
  4. washwashed
  5. customdried at 60° C. in air
  6. customIt can be purified by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-cd15767428464b529e5d84d862f38c56
Source dataset
uspto-grants-1977_06
Patent number
US04031103

Reaction notes

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