Phosphorus oxychloride → (3-Bromo-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943644Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[Br:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:15](O)=[O:16].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>>[Br:11][C:12]1[CH:13]=[C:14]([C:15]([N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:10]=[CH:9][N:8]=[CH:7][C:3]2=3)=[O:16])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

Reactant 4

HCID 24813Phosphorus oxychloride

HCID 668363-Bromo-4-methoxybenzoic acid

HCID 516892Sodium Bicarbonate

HCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 66936511(3-Bromo-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

Conditions

Temperature: 100 °C

Procedure

To a mixture of 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (50 mg, 0.37 mmol) and 3-bromo-4-methoxy-benzoic acid (102 mg, 0.44 mmol), phosphorus oxychloride (2 ml) was added and stirred at 100° C. for 12 hours. The reaction mixture was cooled to 0° C., neutralized with saturated solution of sodium hydrogen carbonate to pH of 8-9 and extracted with ethyl acetate.

Workup

additionwas added
temperatureThe reaction mixture was cooled to 0° C.
extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-29afa628e925493d956bef5c02e2ffdd
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394792B2

Reaction notes

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