Ethyl formate → HCID 13983428, compound

HRID 2413946Notes

Reaction equation

HRID 2413946 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:11])=O)[CH:6]=[CH:5][CH:4]=1.[CH:12](OCC)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[N:19]=1.[OH-].[Na+]>Cl.O>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]2[C:20](=[N:24][C:9]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH3:2])[CH:8]=3)=[CH:11][CH:12]=2)[N:19]=1

Participants

8

Reactant 5

HCID 8025Ethyl formateHCID 88612,6-DiaminopyridineHCID 114553-MethylacetophenoneHCID 14798Sodium Hydroxide2×HCID 5360545Sodium

Product 1

HCID 13983428HCID 13983428, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The procedure is analogous to that described in Example 11, but starting with sodium (2.3 g), 3-methylacetophenone (13.4 g) and ethyl formate (11 g). The solid obtained (18.4 g) is then added to 2,6-diaminopyridine (12.1 g). The product obtained after hydrolysis and neutralization with sodium hydroxide (14 g); m.p. approximately 140° C.) is dissolved in concentrated hydrochloric acid (d=1.19; 100 cc). The precipitate obtained after hydrolysis with distilled water (500 cc) followed by neutralization with 10N sodium hydroxide is separated by filtration, washed with distilled water (5×50 cc) and methanol (2×50 cc), and then air-dried. 2-Amino-7-(3-methylphenyl)-1,8-naphthyridine (7.3 g), m.p. 180° C., is obtained.

Workup

  1. customThe solid obtained (18.4 g)
  2. customThe product obtained
  3. customThe precipitate obtained
  4. customis separated by filtration
  5. washwashed with distilled water (5×50 cc) and methanol (2×50 cc)
  6. customair-dried

Sources & evidence

ORD record
ord-97ebd9e7eb614fec8ad2106779df75cd
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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