Water → HCID 18331350, compound

HRID 2270088Notes

Reaction equation

HRID 2270088 reaction equation
C[N+]1([O-])CC[O:5]CC1.[OH2:9].[CH3:10][C:11]1[C:20]([CH3:21])=[CH:19][C:18]2[C:13](=[C:14]([CH:22]=[CH2:23])[CH:15]=[CH:16][CH:17]=2)[N:12]=1>C(O)(C)(C)C.CC(C)=O.[Os](=O)(=O)(=O)=O>[CH3:10][C:11]1[C:20]([CH3:21])=[CH:19][C:18]2[C:13](=[C:14]([CH:22]([OH:5])[CH2:23][OH:9])[CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

7

Reactant 3

HCID 962Water2×HCID 82029Methyl morpholine oxideHCID 15458593HCID 15458593, compound

Product 1

HCID 18331350HCID 18331350, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

1.17 g (10 mmol) of N-methylmorpholine N-oxide, 10 ml of water and 30 ml of acetone are placed in a 100 ml three-necked flask. 0.4 mol of a solution containing 1% by mass of osmium tetroxide in tert-butanol is added dropwise, followed by addition of a solution of 1.4 g (7.6 mmol) of 2,3-dimethyl-8-vinyl-quinoline in 10 ml of acetone. The reaction mixture is stirred for 2 hours at room temperature. 50 ml of water are added and the resulting mixture is extracted with ethyl acetate (3×100 ml). The organic phases are combined, washed with 100 ml of 1% sodium bisulphite solution and 100 ml of 1% sodium bicarbonate solution, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a column of silica (elution solvent: 30% ethyl acetate in cyclohexane). 1.34 g (yield: 81%) of 2,3-dimethyl-8-(1,2-dihydroxyethyl)quinoline are obtained in the form of a white solid. m.p. =120° C.

Workup

  1. additionis added dropwise
  2. extractionthe resulting mixture is extracted with ethyl acetate (3×100 ml)
  3. washwashed with 100 ml of 1% sodium bisulphite solution and 100 ml of 1% sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on a column of silica (elution solvent: 30% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-37eceb2a4ff74884b602d6d8088c8a3d
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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