Hydrochloric Acid → (2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943670Notes

Reaction equation

HRID 1943670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1.Cl>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[OH:8].[O:16]1[CH2:17][CH2:18][N:13]([CH:11]=[O:12])[C:14]2[CH:22]=[N:21][CH:20]=[CH:19][C:15]1=2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 82050Lithium BromideHCID 44608224(3,5-Difluoro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

Product 2

HCID 44608225(3,5-Difluoro-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneHCID 86650558(2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneYield 231.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 10 ml flask, (3,5-difluoro-4-methoxy-phenyl)-(2,3-dihydro -pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (50 g, 0.163 mmol), lithium bromide (57 mg, 0.65 mmol) and piperazine (21 mg, 0.24 mmol) were dissolved with N,N-dimethyl formamide, and stirred at 1000 for 3 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to weak acidic condition (pH=6) by using 1N hydrochloric acid, and the formed solid was filtered and washed with distilled water and ethyl acetate. The resulting solid was recrystallized from methanol to obtain the target compound 29, i.e., 3,5-difluoro-4-hydroxy -phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (31 mg, 65%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe formed solid was filtered
  3. washwashed with distilled water and ethyl acetate
  4. customThe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-3f85de2900224204a8f0a4993c156fee
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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