Ethanol → HCID 73473594, compound

HRID 2226969Notes

Reaction equation

HRID 2226969 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][CH:27]=O)[CH:21]=4)[CH2:16]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31].CC[OH:34]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][CH:27]=[N:30][OH:31])[CH:21]=4)[C:16]3=[O:34])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 18963947HCID 18963947, compound

Product 1

HCID 73473594HCID 73473594, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the above aldehyde (~23 mmol) in pyridine (20 ml) and EtOH (20 ml) is added hydroxylamine hydrochloride (3.2 g, 46 mmol). The reaction mixture is stirred overnight. The solvent is removed in vacuo and the residue dissolved in EtOAc (300 ml) and 2N HCl (300 ml). The EtOAc portion is washed with saturated NaHCO3 solution (300 ml), saturated NaCl solution (300 ml), dried over MgSO4, and concentrated in vacuo. The resulting material is purified by chromatography (silica gel 1:9 EtOAc/hexanes, 1:4 EtOAc/hexanes and 2:3 EtOAc/hexanes) yielding α-[2-(4'-fluoro-4-biphenylylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yloxy]-acetaldehyde oxime.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (300 ml)
  3. washThe EtOAc portion is washed with saturated NaHCO3 solution (300 ml), saturated NaCl solution (300 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting material is purified by chromatography (silica gel 1:9 EtOAc/hexanes, 1:4 EtOAc/hexanes and 2:3 EtOAc/hexanes)

Sources & evidence

ORD record
ord-f3d7803ee70345f7b3f94874d411f313
Source dataset
uspto-grants-1994_09
Patent number
US05350761

Reaction notes

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