Hydroxylamine → HCID 178515525, compound

HRID 1717860Notes

Reaction equation

HRID 1717860 reaction equation
[OH:1][NH2:2].[OH-].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([C:12]#[C:13][C:14]([O:16]C)=O)[CH:9]=[CH:10][CH:11]=1>O.CO.C1COCC1>[Br:5][C:6]1[CH:7]=[C:8]([C:12]2[O:1][N:2]=[C:14]([OH:16])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 10681439Methyl 3-(3-bromophenyl)prop-2-ynoate

Product 1

HCID 178515525HCID 178515525, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of hydroxyamine (50% in water, 0.50 mL, 16.3 mmol) in water and NaOH (197 mg, 4.92 mmol) to a solution of methyl 3-(3-bromophenyl)propiolate (980 mg, 4.10 mmol) in a mixture of MeOH and THF (6.0 mL/12.0 mL). Remove the solvents after 2 d. Dissolve the residue in water. Adjust the pH of the aqueous phase to 2 and extract with EtOAc. Dry, filter and concentrate. Purify the residue by flash chromatography eluting with a mixture of EtOAc and hexanes (50:50) to afford the title compound (856 mg, 87%): 1H NMR (d6-DMSO) δ 11.54 (s, 1H), 8.08 (dd, 1H, J=2.0, 1.6 Hz), 7.87 (ddd, 1H, J=8.6, 1.6, 0.8 Hz), 7.75 (ddd, 1H, J=8.2, 2.0, 0.8 Hz), 7.54 (t, 1H, J=7.8 Hz), 6.75 (s, 1H).

Workup

  1. customRemove the solvents after 2 d
  2. dissolutionDissolve the residue in water
  3. extractionextract with EtOAc
  4. customDry
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by flash chromatography
  8. washeluting with a mixture of EtOAc and hexanes (50:50)

Sources & evidence

ORD record
ord-1547b77600f842109f2438aed648ad01
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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