Tin atom → 7-Phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509273Notes

Reaction equation

HRID 1509273 reaction equation
[N+:1]([C:4]1[C:5]([O:16][CH2:17][C:18]([O:20]CC)=O)=[N:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O.[Sn]>Cl>[C:10]1([C:8]2[CH:7]=[N:6][C:5]3[O:16][CH2:17][C:18](=[O:20])[NH:1][C:4]=3[CH:9]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 5352426Tin atomHCID 67255179Ethyl 2-((3-nitro-5-phenylpyridin-2-yl)oxy)acetate

Product 1

HCID 669367437-Phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

In a 500 ml round-bottomed flask was added ethyl 2-(3-nitro-5-phenylpyridin-2-yloxy)acetate (4.6 g, 15.22 mmol) in hydrochloric acid, 37% (40 ml) to give a yellow suspension. The mixture was cooled to 0-5° C. followed by the portion wise addition of tin powder (9.94 g, 84 mmol). The addition proved to be exothermic. Caution should be taken while adding. The mixture was then stirred at room temperature for further 30 minutes until all foaming ceased. The reaction mixture was heated to 80° C. under a nitrogen atmosphere for 3 hours.

Workup

  1. customto give a yellow suspension
  2. additionThe addition
  3. additionwhile adding
  4. temperatureThe reaction mixture was heated to 80° C. under a nitrogen atmosphere for 3 hours

Sources & evidence

ORD record
ord-f13cf9e9ce16442abb54db50a4d6fd1e
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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