3-Nitroaniline → HCID 531958, compound

HRID 1258539Notes

Reaction equation

HRID 1258539 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 74233-NitroanilineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 531958HCID 531958, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-Nitro-phenylamine (5 g, 36.2 mmol) was dissolved in a biphasic mixture of ethyl acetate (100 ml) and aqueous sodium hydrogen carbonate (1N) (100 ml). 4-Fluoro-benzoyl-chloride (8.7 ml, 41.6 mmol) was added under vigorous stirring. The mixture was stirred for 2 hours at ambient temperature. The phases were separated, the organic phase was dried over sodium sulfate and concentrated. The residue was used without further purification (9.4 g, 100% yield). 1H-NMR (CDCl3, 400 MHz) as disclosed in Magnetic Resonance in Chemistry (1997), 35(8), 543-548.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was used without further purification (9.4 g, 100% yield)

Sources & evidence

ORD record
ord-221a40e1e58a41d1a4aaa9902bf25fa9
Source dataset
uspto-grants-2013_06
Patent number
US08466180B2

Reaction notes

Loading…