Sodium Hydroxide → (3-Chloro-4-methoxy-5-nitro-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943647Notes

Reaction equation

HRID 1943647 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[CH2:11][CH2:10][NH:9][C:8]2[CH:12]=[N:13][CH:14]=[CH:15][C:7]1=2.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:28]([O-:30])=[O:29])[C:25]=1[O:26][CH3:27])[C:20](O)=[O:21].[OH-].[Na+]>>[Cl:16][C:17]1[CH:18]=[C:19]([C:20]([N:9]2[CH2:10][CH2:11][O:6][C:7]3[CH:15]=[CH:14][N:13]=[CH:12][C:8]2=3)=[O:21])[CH:23]=[C:24]([N+:28]([O-:30])=[O:29])[C:25]=1[O:26][CH3:27]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 17733363HCID 17733363, compoundHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 66936540(3-Chloro-4-methoxy-5-nitro-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

Procedure

To phosphorus oxychloride (3.00 ml), 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (177 mg, 1.30 mmol) and 3-chloro-4-methoxy-5-nitro benzoic acid (200 mg, 0.87 mmol) were added and then stirred at 95□ for 16 hours. After completion of the reaction, the reaction mixture was poured into ice water and neutralized with saturated solution of sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-7f3e3521fdbb4fb2afff5e4b4465b309
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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