4-Chlorophenol → 2-Amino-7-(4-chlorophenoxy)-1,8-naphthyridine

HRID 2413930Notes

Reaction equation

HRID 2413930 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.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[OH-].[K+]>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:20][C:17]3[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 46844-ChlorophenolHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 137873742-Amino-7-(4-chlorophenoxy)-1,8-naphthyridineYield 73.4%

Conditions

Temperature
140 °C

Procedure

A mixture consisting of 2-amino-7-chloro-1,8-naphthyridine (1.8 g), 4-chlorophenol (12.85 g) and 85% strength potassium hydroxide pellets (1.1 g) is heated for 8 hours at 140° C. The reaction mixture is poured into distilled water (200 cc) and made alkaline to a pH of 10 with 4N sodium hydroxide. The suspension obtained is filtered and washed with distilled water to a pH of approximately 7. The solid obtained is air-dried to give 2-amino-7-(4-chlorophenoxy)-1,8-naphthyridine (2 g), m.p. 177° C.

Workup

  1. additionThe reaction mixture is poured
  2. distillationinto distilled water (200 cc)
  3. customThe suspension obtained
  4. filtrationis filtered
  5. washwashed with distilled water to a pH of approximately 7
  6. customThe solid obtained
  7. customis air-dried

Sources & evidence

ORD record
ord-49aedb545ffe4720bd99602b91be0d78
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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