M-Cresol → HCID 20217516, compound

HRID 235837Notes

Reaction equation

HRID 235837 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][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.[OH-].[K+]>C(OCC)(=O)C>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:20][C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([CH3:13])[CH:15]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217516HCID 20217516, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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-methylphenol (43.2 g) and potassium hydroxide pellets (13.2 g; 85% purity). After treatment with caustic soda and washing, the product produced (21.6 g; m.p. 148° C.) is dissolved in boiling ethyl acetate (200 cc). After 18 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethyl acetate (10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). 2-amino-7-(3-methylphenoxy)-1,8-naphthyridine (9 g) is produced, m.p. 152° C. EXAMPLE 41

Workup

  1. washAfter treatment with caustic soda and washing
  2. customthe product produced (21.6 g; m.p. 148° C.)
  3. dissolutionis dissolved
  4. customthe crystallised solid is separated by filtration
  5. washwashed with ethyl acetate (10 cc)
  6. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-d8a74cf1382f411480140e1e5a5dce50
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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