3-Chloroaniline → HCID 67338426, compound

HRID 1260386Notes

Reaction equation

HRID 1260386 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[C:8](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13].[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:17](=[O:19])/[CH:16]=[CH:15]/[C:8]2[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:6]([OH:5])[CH:7]=2)[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 79323-ChloroanilineHCID 24386Thionyl ChlorideHCID 12125374HCID 12125374, compound

Product 1

HCID 67338426HCID 67338426, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Thionyl chloride (0.83 mL, 6.6 mmol) was added portionwise to a suspension of (E)-3-(3-hydroxy-4-nitro-phenyl)-acrylic acid (1.05 g, 5.0 mmol) in DCM-DMF (20-2 mL). After stirring the resulting solution at RT for 1.5 hrs, 3-chloro-aniline (2.12 mL, 20 mmol) was added dropwise and the mixture was stirred at RT for additional 2 hrs. Then the reaction mixture was diluted with DCM and washed with water, aqueous hydrochloric acid, and brine. The organic layer was dried over sodium sulphate and evaporated. The resulting raw material was purified first by column chromatography (eluant DCM/MeOH), yielding 1.25 g of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for additional 2 hrs
  2. washwashed with water, aqueous hydrochloric acid, and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated
  5. customThe resulting raw material was purified first by column chromatography (eluant DCM/MeOH)

Sources & evidence

ORD record
ord-422a9217fcac42779b0a2b793dca9522
Source dataset
uspto-grants-2013_06
Patent number
US08470831B2

Reaction notes

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