(NZ)-N-(2-bromofluoren-9-ylidene)hydroxylamine → HCID 178517106, compound

HRID 1423365Notes

Reaction equation

HRID 1423365 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](=[N:15]/O)/[C:4]=2[CH:3]=1.BrC1C=CC2C(C=1)=NC([OH:32])=C1C=2C=CC=C1>O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:4](=[C:5]([OH:32])[N:15]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH:3]=1

Participants

4

Reactant 2

HCID 6187985(NZ)-N-(2-bromofluoren-9-ylidene)hydroxylamine2×HCID 178516985HCID 178516985, compound

Product 1

HCID 178517106HCID 178517106, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
185 °C

Procedure

To the solid product from Step 1, (9Z)-2-bromo-9H-fluoren-9-one oxime (106 mg, 0.387 mmol) was added polyphosphoric acid (5 g). The mixture was then heated to 185° C. for 2 h. After cooling to r.t., water was added and the resulting solid was collected by filtration to give a 1:1 mixture of the title compounds and the regioisomeric 3-bromophenanthridin-6-ol. LRMS (M+H)+=274.2.

Workup

  1. temperatureAfter cooling to r.t.
  2. filtrationthe resulting solid was collected by filtration
  3. customto give

Sources & evidence

ORD record
ord-0bdd7744e82e4d37a7c771517237496f
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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