P-Chloroacetophenone → HCID 13983422, compound

HRID 2413933Notes

Reaction equation

HRID 2413933 reaction equation
[Na].[CH3:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.[CH:12](OCC)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[N:19]=1.[OH-].[Na+]>>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]2[C:20](=[N:24][C:3]([C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=3)=[CH:2][CH:12]=2)[N:19]=1

Participants

6

Reactant 5

HCID 7467P-ChloroacetophenoneHCID 8025Ethyl formateHCID 88612,6-DiaminopyridineHCID 14798Sodium HydroxideHCID 5360545Sodium

Product 1

HCID 13983422HCID 13983422, compoundYield 88.2%

Procedure

The procedure is analogous to that described in Example 11, but starting with sodium (2.3 g), 4-chloroacetophenone (15.5 g) and ethyl formate (11 g). The solid obtained (20.4 g) is then added to 2,6-diaminopyridine (11.6 g). The product obtained after hydrolysis and neutralization with sodium hydroxide is separated by filtration, washed with distilled water (6×100 cc) at a temperature in the vicinity of 50° C., and then air-dried. 2-Amino-7-(4-chlorophenyl)-1,8-naphthyridine (22.6 g), m.p. approximately 130° C., is thus obtained.

Workup

  1. customThe solid obtained (20.4 g)
  2. customThe product obtained
  3. customis separated by filtration
  4. washwashed with distilled water (6×100 cc) at a temperature in the vicinity of 50° C.
  5. customair-dried

Sources & evidence

ORD record
ord-cd33a52a58a74291a98272906e2140cf
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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