2-Nitrophenol → Acetamide, N-(3-fluoro-4-hydroxyphenyl)-

HRID 2373952Notes

Reaction equation

HRID 2373952 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].[N+]([C:15]1C=CC=C[C:16]=1[OH:21])([O-])=O.C(OC(=O)C)(=O)C>C(O)(=O)C.O=[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:16](=[O:21])[CH3:15])[CH:5]=[CH:4][C:3]=1[OH:11]

Participants

6

Reactant 3

HCID 69472-NitrophenolHCID 7918Acetic AnhydrideHCID 98252-Fluoro-4-nitrophenol

Product 1

HCID 3014069Acetamide, N-(3-fluoro-4-hydroxyphenyl)-

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

The title compound was prepared from the commercially available 2-fluoro-4-nitrophenol according the procedure of Burckhalter, J. H. et al. (J. Am. Chem. Soc. 1948, 70, 1363). Nitrophenol (5.73 g, 36.5 mmol) and acetic anhydride (3.72 g, 36.5 mmol) were dissolved in acetic acid (20 mL) and PtO2 (150 mg) was then added. The reaction mixture was shaken under H2 atmosphere (50 psi) at RT for 24 h. The precipitate which formed was collected by vacuum filtration and the filter paper was washed with acetic acid (25 mL). The combined filtrate and washing was concentrated in vacuo to give the title compound (2.0 g). The solid that remained on the filter paper was treated with MeOH to dissolve the product and the Pt2O filtered off. The filtrate was concentrated in vacuo and the solid obtained was triturated with 1:1 EtOAc/hexanes (200 mL) to give a second crop of the title compound (1.8 g, 62% overall). 1H NMR (DMSO-d6) δ 9.83 (s, 1H), 9.51 (s, 1H), 7.50 (dd, 1H, J=13.6, 2.5 Hz), 7.03 (d, 1H, J=8.5 Hz), 6.84 (dd, 1H, J=9.3, 9.3 Hz), 1.98 (s, 3H); MS(ESI+) m/z 170.23 (M+H)+.

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by vacuum filtration
  3. washthe filter paper was washed with acetic acid (25 mL)
  4. washThe combined filtrate and washing
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-a2c3ccc4d8814ae3ac76abc67d834cda
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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