3-Methoxyphenol → HCID 20217497, compound

HRID 235841Notes

Reaction equation

HRID 235841 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.[OH-].[K+]>C(O)C>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:21][C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217497HCID 20217497, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 4, but starting with 2-amino-7-chloro-1,8-naphthyridine (17.95 g), 3-methoxyphenol (49.6 g) and potassium hydroxide pellets (13.2 g; 85% purity). After treatment with caustic soda and washing, the product produced (23.8 g; m.p. 156° C.) is dissolved in boiling ethanol (200 cc). After 18 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). 2-Amino-7-(3-methoxyphenoxy)-1,8-naphthyridine (17.7 g) is produced, m.p. 160° C.

Workup

  1. washAfter treatment with caustic soda and washing
  2. customthe product produced (23.8 g; m.p. 156° C.)
  3. dissolutionis dissolved
  4. customthe crystallised solid is separated by filtration
  5. washwashed with ethanol (10 cc)
  6. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-0d8b68d6f1e940ffb52eeadefcb627ed
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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