Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylate → 2-fluoro-5-hydroxyphenanthridin-6(5H)-one

HRID 238071Notes

Reaction equation

HRID 238071 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=O)=[C:6]([C:8]2[C:9]([C:14](OC)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:18]([OH:20])[C:14](=[O:15])[C:9]3[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 67296936Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 672967442-fluoro-5-hydroxyphenanthridin-6(5H)-oneYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product of Example 37a (methyl 5′-fluoro-2′-nitrobiphenyl-2-carboxylate, 56.79 mg, 0.206 mmol) in methanol (9 mL) was added 10% palladium on carbon (15.6 mg, 0.015 mmol). The flask was fitted with a hydrogen balloon and de-gassed three times with hydrogen. The reaction mixture was stirred, diluted with dimethylformamide, and filtered. The filtrate was concentrated to provide 2-fluoro-5-hydroxyphenanthridin-6(5H)-one (37b, 46.36 mg, 0.202 mmol, 98% yield).

Workup

  1. customde-gassed three times with hydrogen
  2. additiondiluted with dimethylformamide
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a74fee822c9f4d049562a931836b5850
Source dataset
uspto-grants-2014_02
Patent number
US08642538B2

Reaction notes

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