3-Nitroaniline → HCID 59804275, compound

HRID 422024Notes

Reaction equation

HRID 422024 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:13][O:14][C:15](=[O:31])[CH:16]([C:21]1[CH:26]=[C:25](F)[CH:24]=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29])[C:17]([O:19][CH3:20])=[O:18].[NH4+].[Cl-]>CS(C)=O>[CH3:13][O:14][C:15](=[O:31])[CH:16]([C:21]1[CH:26]=[C:25]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:24]=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29])[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 74233-NitroanilineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10038811HCID 10038811, compound

Product 1

HCID 59804275HCID 59804275, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 3-nitro-phenylamine (2.08 g, 15.1 mmol) in DMSO (40 ml) is added NaH (60% dispersion in mineral oil, 0.60 g, 15 mol). The reaction is stirred at this temperature for 30 minutes. After that, a solution of 2-(5-fluoro-2-nitro-phenyl)-malonic acid dimethyl ester (1.36 g, 5.02 mmol) in DMSO (10 ml) is added slowly. The reaction is stirred at 80° C. for 24 hours, and is poured into a saturated solution of NH4Cl (150 ml). The mixture is extracted with ethyl acetate (100 ml×3). The insoluble is filtered off. The organic layers are combined, dried and concentrated. The desired ester is obtained after flash column chromatography purification (silica gel, eluted by hexanes-ethyl acetate): LC-MS: 390.1 (MH+).

Workup

  1. stirringThe reaction is stirred at 80° C. for 24 hours
  2. extractionThe mixture is extracted with ethyl acetate (100 ml×3)
  3. filtrationThe insoluble is filtered off
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94ec99e6933c4cadbf1cba6bd0de4ac9
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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