Hydroxyamine hydrochloride → (NZ)-N-(2-bromofluoren-9-ylidene)hydroxylamine

HRID 1423364Notes

Reaction equation

HRID 1423364 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=O)[C:4]=2[CH:3]=1.Cl.[NH2:17][OH:18]>CCO.O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)/[C:5](=[N:17]/[OH:18])/[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 7258312-Bromo-9-fluorenone

Product 1

HCID 6187985(NZ)-N-(2-bromofluoren-9-ylidene)hydroxylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-bromo-9H-fluoren-9-one (100 mg, 0.39 mmol) in EtOH (10 mL) and water (3 mL) was added hydroxylamine hydrochloride (54 mg, 0.77 mmol). The mixture was then heated to reflux for 1 h. The solvent was then removed in vacuo, and to the residue was added aqueous NaHCO3. The solid was then filtered and dried to give the title product. LRMS (M+H)+ 274.2.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was then removed in vacuo
  4. additionto the residue was added aqueous NaHCO3
  5. filtrationThe solid was then filtered
  6. customdried

Sources & evidence

ORD record
ord-6d39cd9a1bf84ea784317ba2e39499f6
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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