2-Bromophenol → HCID 20217501, compound

HRID 235835Notes

Reaction equation

HRID 235835 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.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].[OH-].[K+]>>[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[Br:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 72442-BromophenolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217501HCID 20217501, compoundYield 36.9%

Conditions

Temperature
120 °C

Procedure

The procedure is similar to that described in Example 4, but starting with 2-amino-7-chloro-1,8-naphthyridine (19.7 g), 2-bromophenol (81.5 g) and potassium hydroxide pellets (15.15 g; 85% purity). After 10 hours' heating at 120° C. and treatment under the conditions described above in Example 4, the product produced (21.5 g; m.p. 160° C.) is purified by chromatography on a column 45 mm in diameter containing silica (300 g; 0.040-0.063 mm), eluting with a mixture (95:5 by volume) of methylene chloride and methanol and collecting 100-cc fractions. After concentration to dryness of the fractions 2 to 10 at 40° C. under reduced pressure (4 kPa), 2-amino-7-(2-bromophenoxy)-1,8-naphthyridine (12.8 g) is produced, m.p. 206° C.

Workup

  1. customthe product produced (21.5 g; m.p. 160° C.)
  2. customis purified by chromatography on a column 45 mm in diameter
  3. additioncontaining silica (300 g; 0.040-0.063 mm)
  4. washeluting with a mixture (95:5 by volume) of methylene chloride and methanol
  5. customcollecting 100-cc fractions
  6. concentrationAfter concentration to dryness of the fractions 2 to 10 at 40° C. under reduced pressure (4 kPa)

Sources & evidence

ORD record
ord-1637bf43e77b4a2abdf3ff5d8d872877
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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