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

HRID 404143Notes

Reaction equation

HRID 404143 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-bcde7b55d40c4f35b6b87ec2d17509ef
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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