Hydroxylamine → HCID 46852454, compound

HRID 523904Notes

Reaction equation

HRID 523904 reaction equation
[OH:1][NH2:2].C([O:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C>CO.CN(C=O)C>[OH:1][NH:2][C:6](=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 58545067HCID 58545067, compound

Product 1

HCID 46852454HCID 46852454, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 4 mL) was added to II (120 mg, 0.3 mmol) in MeOH (4 mL) and DMF (2 mL) at rt. The reaction mixture was stirred for 24 h, after which the solvents were evaporated under reduced pressure. The resulting residue was dissolved and co-evaporated with toluene (3×5 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:2 to 100:8) to furnish III as a yellow oil (28 mg, 23%).

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 (100:2 to 100:8)

Sources & evidence

ORD record
ord-1803779be41b4e239d8ba4a369bdcd5e
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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