3-Hydroxypyridine → HCID 20217520, compound

HRID 235842Notes

Reaction equation

HRID 235842 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.[OH:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[OH-].[K+]>O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217520HCID 20217520, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 (17.9 g), 3-hydroxypyridine (38 g) and potassium hydroxide pellets (11,2 g; 85% purity). The product produced by precipitation in water and extraction with ethyl acetate (4.7 g) is dissolved in boiling ethyl acetate (80 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethyl ether (2×5 cc) and dried in the air at 20° C. 2-Amino-7-(3-pyridyl)oxy-1,8-naphthyridine (2.1 g) is produced, m.p. 178° C.

Workup

  1. extractionextraction with ethyl acetate (4.7 g)
  2. dissolutionis dissolved
  3. customthe crystallised solid is separated by filtration
  4. washwashed with ethyl ether (2×5 cc)
  5. customdried in the air at 20° C

Sources & evidence

ORD record
ord-fb5a09b275214ba6b3a5cfb563cb49c4
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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