O-Phenylenediamine → HCID 178517134, compound

HRID 1429090Notes

Reaction equation

HRID 1429090 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10](=O)[C:11]([O:13]CC)=O.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23]>CCO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11]([OH:13])=[N:23][C:18]2[C:17]([N:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 18370915HCID 18370915, compound

Product 1

HCID 178517134HCID 178517134, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 2-(benzofuran-2-yl)-2-oxoacetate (Example 15a, 237 mg, 1.09 mmol) in EtOH (2.7 mL) was added o-phenylenediamine (117 mg, 1.09 mmol). The reaction mixture was stirred at 90° C. for 16 h (a yellow solid appeared quickly). The mixture was cooled to 0° C., filtered, and the solid rinsed with cold EtOH. The yellow solid was azeotroped with CHCl3 and benzene and dried to provide the title compound (268 mg, 94% yield).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationfiltered
  3. washthe solid rinsed with cold EtOH
  4. customThe yellow solid was azeotroped with CHCl3 and benzene
  5. customdried

Sources & evidence

ORD record
ord-7bfce7dcd7ad493b9838acbd7ad4f280
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

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