3-Chloroaniline → HCID 24956350, compound

HRID 606369Notes

Reaction equation

HRID 606369 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:14])O[C:11](=[O:13])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(O)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([N:19]2[C:11](=[O:13])[CH:12]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[C:9]2=[O:14])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 14958697HCID 14958697, compound

Product 1

HCID 24956350HCID 24956350, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (3-methylphenyl)-furan-2,5-dione (265 mg, 1.41 mmol) in acetic acid (5 ml) at room temperature was added 3-chloroaniline (149 μl, 1.41 mmol). The reaction mixture was heated to reflux and stirred for 3 hours. The reaction mixture was cooled to room temperature. The precipitate formed was filtered, re-suspended in water (15 ml) and recovered by filtration. The precipitate was washed with water (10 ml), heptane (10 ml) and dried under air suction followed by high vacuum.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. filtrationrecovered by filtration
  6. washThe precipitate was washed with water (10 ml), heptane (10 ml)
  7. customdried under air suction

Sources & evidence

ORD record
ord-64dbc2181de448cea34382540f620b95
Source dataset
uspto-grants-2011_03
Patent number
US07915304B2

Reaction notes

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