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Methyl morpholine oxide → 1-(8-Bromoquinolin-2-yl)ethane-1,2-diol

HRID 1041956
Notes
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Reaction equation

HRID 1041956 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=C(C=C)[CH:8]=[CH:7]2.C[N+]1([O-])CC[O:18]CC1.[CH3:22][C:23]([CH3:25])=[O:24].O>ClCCl.O=[Os](=O)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:22]([CH:23]([OH:24])[CH2:25][OH:18])[CH:8]=[CH:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 672347808-Bromo-2-vinylquinoline

Product 1

HCID 672345141-(8-Bromoquinolin-2-yl)ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
Dichloromethane
Solvent

Procedure

To 8-bromo-2-vinylquinoline (0.886 g, 3.78 mmol) in acetone/H2O (8 mL/2 mL) was added 4-methylmorpholine N-oxide (1.06 g, 4.54 mmol) followed by OsO4 (0.5 mL, 2.5% in t-BuOH). The reaction mixture was stirred for two hours at ambient temperature then diluted with dichloromethane. The organic layer was washed with saturated sodium sulfate and brine and concentrated to give crude product.

Workup

  1. washThe organic layer was washed with saturated sodium sulfate and brine
  2. concentrationconcentrated
  3. customto give crude product

Sources & evidence

ORD record
ord-10c4ca74f28442ce835b3cd9e3e5d290
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557809B2

Reaction notes

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