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Water → 1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine hydrochloride

HRID 1428201
Notes
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Reaction equation

HRID 1428201 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:10]=[C:9]([N+]([O-])=O)[CH:8]=[C:7](Cl)[C:5]=1N.F[C:16]1[C:23]([C:24]#N)=[C:22](F)[C:21](F)=C(F)C=1C#N.O.[CH3:30][N:31]([CH:33]=O)[CH3:32]>>[CH3:30][N:31]1[CH2:33][CH:16]=[C:23](/[CH:22]=[CH:21]/[C:4]2[C:5]3[C:7](=[CH:10][CH:4]=[CH:5][CH:7]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:24][CH2:32]1.[ClH:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 74302,6-Dichloro-4-nitroanilineHCID 14798Sodium HydroxideHCID 608182Tetrafluoroisophthalonitrile

Product 1

HCID 64441431-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine hydrochloride

Procedure

3.12 g (0.078 mol) of sodium hydroxide was added to a solution of 8.07 g (0.039 mol) of 2,6-dichloro-4-nitroaniline in 60 mL of DMF, followed by addition of 7.80 g (0.039 mol) of 2,4,5,6-tetrafluoroisophthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:5, as an eluent) to give 8.08 g of compound B-115 as yellowish solid, m.p. 164-166° C.

Workup

  1. stirringthe mixture was stirred for 5 h
  2. additionafter addition at room temperature
  3. extractionextracted with ethyl acetate
  4. washthe organic phase was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:5

Sources & evidence

ORD record
ord-6d6989ff70144543869194681668b900
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937072B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes