Hydrogen Bromide → 4-Hydroxy-6-fluorophenanthridine

HRID 581213Notes

Reaction equation

HRID 581213 reaction equation
C[O:2][C:3]1[C:16]2[C:7](=[C:8]3[C:13](=[C:14]([F:17])[N:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:6]=[CH:5][CH:4]=1.Br.C(=O)([O-])[O-].[Na+].[Na+]>>[OH:2][C:3]1[C:16]2[C:7](=[C:8]3[C:13](=[C:14]([F:17])[N:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 544641604-Methoxy-6-fluorophenanthridine

Product 1

HCID 541652404-Hydroxy-6-fluorophenanthridineYield 96.8%

Procedure

A mixed solution comprising 115 mg of 4-methoxy-6-fluorophenanthridine and 5 ml of 48% hydrobromic acid was allowed to react at 116° C. for a period of 14 hr. After the completion of the reaction, the reacted solution was introduced into an aqueous solution of sodium carbonate and the product was extracted by ethyl acetate. After ethyl acetate was distilled away, the residue was purified by column chromatography to obtain 104.5 mg of 4-hydroxy-6-fluorophenanthridine on recrystallization from hexane (yield 96.9%).

Workup

  1. customto react at 116° C. for a period of 14 hr
  2. customAfter the completion of the reaction
  3. extractionthe product was extracted by ethyl acetate
  4. distillationAfter ethyl acetate was distilled away
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-242d72649d2648c380bcd1e144f7279b
Source dataset
uspto-grants-1999_07
Patent number
US05919928

Reaction notes

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