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

HRID 523900Notes

Reaction equation

HRID 523900 reaction equation
[OH:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](OCC)=[O:17]>CO>[OH:1][NH:2][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[C:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58545040Ethyl 8,8-bis(pyridin-2-yl)octanoate

Product 1

HCID 46852451n-Hydroxy-8,8-di(pyridin-2-yl)oct-7-enamideYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HONH2 (50% aqueous, 1 mL) was added to II (34 mg, 0.1 mmol) in MeOH (1 mL) at rt. The reaction mixture was stirred for 48 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 (100:3 to 100:5) to furnish III as a colourless oil (16 mg, 52%).

Workup

  1. customafter which the solvents were evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved
  3. customthen was purified by silica gel column chromatography
  4. washeluting with CH2Cl2/MeOH (100:3 to 100:5)

Sources & evidence

ORD record
ord-23332f0dc9f84b658044b6fbe7fa028c
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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