2-Fluorophenol → HCID 20217539, compound

HRID 235828Notes

Reaction equation

HRID 235828 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6](Cl)=[CH:7][CH:8]=2)[N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].[OH-].[K+]>C(O)C>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[F:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217539HCID 20217539, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 37, but starting with 2-amino-7-chloro-1,8-naphthyridine (18 g), 2-fluorophenol (44.8 g) and potassium hydroxide pellets (13.2 g; 85% purity). After treatment with caustic soda and washing, the product produced (24 g; m.p. 202° C.) is dissolved in boiling ethanol (200 cc). After 16 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×15 cc) and dried at 40° C. under reduced pressure (0.067 kPa). 2-Amino-7-(2-fluorophenoxy)-1,8-naphthyridine (14.9 g) is produced, m.p. 206° C.

Workup

  1. washAfter treatment with caustic soda and washing
  2. customthe product produced (24 g; m.p. 202° C.)
  3. dissolutionis dissolved
  4. customthe crystallised solid is separated by filtration
  5. washwashed with ethanol (2×15 cc)
  6. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-4ed7c62a3b6340d280c753bb6995acab
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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