Trifluoroacetic acid → HCID 23335385, compound

HRID 903874Notes

Reaction equation

HRID 903874 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH2:13][CH3:14])[N:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)[CH3:2].FC(F)(F)C(O)=[O:18].N([O-])=O.[Na+].[OH-].[NH4+]>>[CH2:1]([C:3]1[CH:12]=[C:11]([CH2:13][CH3:14])[N:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:18])[NH:8]2)[CH3:2]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 23668193Sodium NitriteHCID 86736245HCID 86736245, compound

Product 1

HCID 23335385HCID 23335385, compound

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of 2-amino-,5,7-diethyl-1,8-naphthyridine (7.0 g., 0.035 mole) in 45 ml. of trifluoroacetic acid is added sodium nitrite (2.66 g., 0.0385 mole) in small portions over 1 hour at -5° C. The mixture is stirred at -5° C. for 2 hours and for an additional hour at room temperature. The reaction mixture is poured into 300 g. of crushed ice and is made alkaline with a slight excess of concentrated ammonium hydroxide. A yellow solid separates and is filtered and washed with a little ice water. Recrystallization from ethyl acetate affords 5,7-diethyl-1,8-naphthyridin-2-(1H)-one melting at 159°-161° C.

Workup

  1. additionThe reaction mixture is poured into 300 g
  2. filtrationA yellow solid separates and is filtered
  3. washwashed with a little ice water
  4. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8e6c2444cee5433783f0c4e761989487
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Reaction notes

Loading…