2-Chloroaniline → HCID 9946949, compound

HRID 1743152Notes

Reaction equation

HRID 1743152 reaction equation
C(O[C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18])C.[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24].C(OC(=O)C)C>CS(C)=O>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH:24][C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18]

Participants

5

Reactant 3

HCID 72402-ChloroanilineHCID 8857Ethyl AcetateHCID 222385043-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione

Product 1

HCID 9946949HCID 9946949, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione (0.38 g, 1.37 mmol) and 2-chloroaniline (0.23 mL, 2.2 mmol) in 2 mL DMSO was heated at 110° C. for overnight. The reaction mixture was cooled to room temperature, and ethylacetate was added, and a precipitate formed. The filtrate was partitioned between ethylacetate and water. The organic layer was dried over sodium sulfate and concentrated. Recrystalized from ethylacetate and hexanes, 203 mg (41%) of 3-(2-chloroanilino)-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione was obtained. LCMS(H+) 360.

Workup

  1. customa precipitate formed
  2. customThe filtrate was partitioned between ethylacetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customRecrystalized from ethylacetate and hexanes

Sources & evidence

ORD record
ord-1dc49b3fc2ba4802bc8bd61dd3fdc111
Source dataset
uspto-grants-2006_03
Patent number
US07008962B2

Reaction notes

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