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

HRID 404144Notes

Reaction equation

HRID 404144 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-f6e4d04d8f4a423bbd376a7528ab4334
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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