(4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone → [5-(4-Amino-2,6-dimethylphenoxy)-2-hydroxyphenyl](4-fluorophenyl)methanone

HRID 1609738Notes

Reaction equation

HRID 1609738 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-])=O)=[CH:19][C:18]=3[CH3:27])[CH:13]=[CH:12][C:11]=2[OH:28])=[O:9])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pt]>[NH2:24][C:20]1[CH:21]=[C:22]([CH3:23])[C:17]([O:16][C:14]2[CH:13]=[CH:12][C:11]([OH:28])=[C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:9])[CH:15]=2)=[C:18]([CH3:27])[CH:19]=1

Participants

4

Reactant 1

HCID 9999865(4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

Product 1

HCID 10020835[5-(4-Amino-2,6-dimethylphenoxy)-2-hydroxyphenyl](4-fluorophenyl)methanone

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone (62.8g, 0.16 mol) is dissolved in ethyl acetate (4L) and hydrogenated at atmospheric pressure over 5% platinum on carbon (13.2g). When the theoretical amount of hydrogen is consumed, the hydrogenation is stopped, the catalyst is filtered off, and the ethyl acetate solution is concentrated to dryness at 50°/3mm Hg. The residue is triturated hot with isopropanol (1L) and collected to yield [5-(4-amino-2,6-dimethylphenoxy)-2-hydroxyphenyl](4-fluorophenyl)methanone, m.p. 198°-202°.

Workup

  1. customWhen the theoretical amount of hydrogen is consumed
  2. filtrationthe catalyst is filtered off
  3. concentrationthe ethyl acetate solution is concentrated to dryness at 50°/3mm Hg
  4. customThe residue is triturated hot with isopropanol (1L)
  5. customcollected

Sources & evidence

ORD record
ord-dd70fc6b2e0a43989db1a3f5e83fe652
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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