Hydroxyamine hydrochloride → HCID 136167206, compound

HRID 646529Notes

Reaction equation

HRID 646529 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH:21]=[O:22])[C:13]([OH:20])=[C:14]([Cl:19])[CH:15]=3)[O:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:24]O>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:24][O:18][C:17]=2[C:16]2[C:11]([OH:10])=[C:12]([C:13]([OH:20])=[C:14]([Cl:19])[CH:15]=2)[CH:21]=[O:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58732641HCID 58732641, compound

Product 1

HCID 136167206HCID 136167206, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(4-bromo-phenyl)-6-chloro-7-hydroxy-4-oxo-4H-chromene-8-carbaldehyde 53.5 mg, 0.14 mmol) in EtOH (6 ml), hydroxylamine hydrochloride (100 mg, 1.4 mmol) was added. The resulting mixture was heated at reflux for 16 hours. EtOH was evaporated and EtOAc (20 ml) was added. The organic layer was washed with sat. NaHCO3 and dried. Solids (33 mg) were obtained when the resulting oil was triturated with ether. 1H NMR (d6-DMSO) δ=9.83 (1H, s); 8.70 (1H, s); 8.21 (1H, s); 7.78 (2H, d) and 7.68 (2H, s). LCMS: (M+1)+=394.1 (RT=8.60 min.)

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 16 hours
  3. customEtOH was evaporated
  4. additionEtOAc (20 ml) was added
  5. washThe organic layer was washed with sat. NaHCO3
  6. customdried

Sources & evidence

ORD record
ord-d2f797fb05c84b07a0998da15fc4f25c
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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