O-Cresol → HCID 20217512, compound

HRID 235836Notes

Reaction equation

HRID 235836 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:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].[OH-].[K+]>C(#N)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[CH3:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 335O-CresolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217512HCID 20217512, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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), 2-methylphenol (43.2 g) and potassium hydroxide pellets (13.2 g; 85% purity). After treatment with caustic soda and washing, the product obtained (21.2 g; m.p. 188° C.) is dissolved in boiling acetonitrile (100 cc). After 4 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). 2-Amino-7-(2-methylphenoxy)-1,8-naphthyridine (15.6 g) is produced, m.p. 192° C.

Workup

  1. washAfter treatment with caustic soda and washing
  2. customthe product obtained (21.2 g; m.p. 188° C.)
  3. dissolutionis dissolved
  4. customthe crystallised solid is separated by filtration
  5. washwashed with acetonitrile (10 cc)
  6. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-6252ba3b77ff4f92ab0867dc5e2aedbd
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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