HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 339669
Notes
Print preview

Reaction equation

HRID 339669 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-83569c5c335942f6a730f427507aee7c
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895550B2

Reaction notes

Loading…