4-Chloroaniline → HCID 12093166, compound

HRID 2087005Notes

Reaction equation

HRID 2087005 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]1([CH:15]=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[OH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](=[O:35])[CH2:27][C:28](=[O:34])[C:29]([O:31]CC)=O)=[CH:20][CH:19]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:15]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:27]([C:26](=[O:35])[CH2:25][CH2:24][C:21]3[CH:20]=[CH:19][C:18]([OH:17])=[CH:23][CH:22]=3)=[C:28]([OH:34])[C:29]2=[O:31])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 16275CyclohexanecarboxaldehydeHCID 12984123HCID 12984123, compound

Product 1

HCID 12093166HCID 12093166, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirring solution of p-chloraniline (320 mg, 2.5 mmol) in 2.5 mL of acetic acid at room temperature, are added cyclohexane carboxaldehyde (0.30 mL, 2.5 mmol) and ethyl 6-(4-hydroxyphenyl)-2,4-dioxohexanoate (618 mg, 2.5 mmol). The reaction mixture is stirred at room temperature. After 30 minutes a white precipitate is formed. The solvent is removed under reduced pressure and the crude material recrystallized from a mixture of ether/methanol. The final compound is collected after filtration as a white crystalline solid m.p. 259° C.

Workup

  1. customAfter 30 minutes a white precipitate is formed
  2. customThe solvent is removed under reduced pressure
  3. customthe crude material recrystallized from a mixture of ether/methanol
  4. customThe final compound is collected
  5. filtrationafter filtration as a white crystalline solid m.p. 259° C.

Sources & evidence

ORD record
ord-f813c50a60084a2a985606afce21581c
Source dataset
uspto-grants-2004_04
Patent number
US06727275B2

Reaction notes

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