2,6-Dimethylphenol → HCID 20217518, compound

HRID 235839Notes

Reaction equation

HRID 235839 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]=[C:16]([CH3:20])[C:15]=1[OH:21].[OH-].[K+]>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:21][C:15]3[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:14]=3[CH3:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 113352,6-DimethylphenolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217518HCID 20217518, compoundYield 80%

Procedure

The procedure is similar to that described in Example 4, but starting with 2-amino-7-chloro-1,8-naphthyridine (17.95 g), 2,6-dimethylphenol (48.6 g) and potassium hydroxide pellets (13.2 g; 85% purity). After treatment with caustic soda and washing, the product produced (24.8 g; m.p. 204° C.) is purified by chromatography on a column 45 mm in diameter containing silica (360 g; 0.040-0.063 mm), eluting with pure methylene chloride and collecting 100-cc fractions. After concentration to dryness of fractions 1 to 48 at 40° C. under reduced pressure (4 kPa), 2-amino-7-(2,6-dimethylphenoxy)-1,8 naphthyridine (21.2 g) is produced, m.p. 218° C.

Workup

  1. washAfter treatment with caustic soda and washing
  2. customthe product produced (24.8 g; m.p. 204° C.)
  3. customis purified by chromatography on a column 45 mm in diameter
  4. additioncontaining silica (360 g; 0.040-0.063 mm)
  5. washeluting with pure methylene chloride
  6. customcollecting 100-cc fractions
  7. concentrationAfter concentration to dryness of fractions 1 to 48 at 40° C. under reduced pressure (4 kPa)

Sources & evidence

ORD record
ord-fb2e9bc1b3f346fa98856870c3669d82
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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