2-Aminophenol → 4-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilide

HRID 74173

Reaction equation

HRID 74173 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].Cl.C(N=C=N[CH2:28][CH2:29][CH2:30]N(C)C)C.C(N([CH2:39][CH3:40])CC)C.[CH:41](Cl)(Cl)Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[C:28]2[CH:29]=[CH:30][CH:40]=[CH:39][CH:41]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 5

HCID 58012-AminophenolHCID 6212ChloroformHCID 8471TriethylamineHCID 679874-Fluoro-3-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 674979344-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilideYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzoic acid (2.00 g, 10.8 mmol) in chloroform (40 mL) was added 2-aminophenol (1.18 g, 10.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.17 g, 11.3 mmol), and triethylamine (1.15 g, 11.3 mmol), and this was stirred at room temperature for 2.5 hours. After the reaction was complete, this was diluted by adding ethyl acetate, and this was washed with water, 1N hydrochloric acid, and saturated aqueous sodium hydrogen carbonate. The organic layer obtained was dried over anhydrous sodium sulfate, after which it was filtered and concentrated to yield the title compound (2.02 g, 68% yield) as orange crystals.

Workup

  1. additionthis was diluted
  2. washthis was washed with water, 1N hydrochloric acid, and saturated aqueous sodium hydrogen carbonate
  3. customThe organic layer obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationafter which it was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e51a015c6d30428c8a4b915518a238cb
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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