Hydroxylamine → HCID 46852610, compound

HRID 523917Notes

Reaction equation

HRID 523917 reaction equation
[OH:1][NH2:2].C(O[C:6](=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[N:21]=[CH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C>CN(C=O)C.CO>[OH:1][NH:2][C:6](=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[N:21]=[CH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 58545030HCID 58545030, compound

Product 1

HCID 46852610HCID 46852610, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 1 mL) was added to II (40 mg, 0.1 mmol) in DMF (0.5 mL) and MeOH (1 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 (2×2 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:3 to 100:8) to furnish III as a colourless oil (19 mg, 54%).

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 100:8)

Sources & evidence

ORD record
ord-d61df47174ba48a6abf78ed4a6380ea3
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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