Hydroxylamine → n-Hydroxy-8,8-di(pyridin-2-yl)oct-7-enamide

HRID 523899Notes

Reaction equation

HRID 523899 reaction equation
[OH:1][NH2:2].C([O:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C>CO>[OH:1][NH:2][C:6](=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 585450338,8-Di-pyridin-2-yl-oct-7-enoic acid ethyl ester

Product 1

HCID 46852451n-Hydroxy-8,8-di(pyridin-2-yl)oct-7-enamideYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HONH2 (50% aqueous, 0.5 mL) was added to II (68 mg, 0.21 mmol) in MeOH (0.5 mL) at rt. The reaction mixture was stirred for 72 h, after which the solvents were evaporated under reduced pressure. The resulting residue was dissolved and co-evaporated with toluene (2×5 mL), then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:1 to 100:10) to furnish III as a colourless oil (12 mg, 18%).

Workup

  1. customafter which the solvents were evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved
  3. customwas purified by silica gel column chromatography
  4. washeluting with CH2Cl2/MeOH (100:1 to 100:10)

Sources & evidence

ORD record
ord-fe1557d9fc984806af22348141a2f0ce
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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