4-Aminophenylacetic acid → HCID 86755325, compound

HRID 1004525Notes

Reaction equation

HRID 1004525 reaction equation
[C:1]([CH2:4][NH:5][C:6]1[C:7]([I:22])=[C:8]([C:19](Cl)=[O:20])[C:9]([I:18])=[C:10]([NH:13][CH2:14][C:15](=[O:17])[CH3:16])[C:11]=1[I:12])(=[O:3])[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:25]=1>CC(N(C)C)=O>[C:1]([CH2:4][NH:5][C:6]1[C:7]([I:22])=[C:8]([C:19]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:28][CH:29]=2)=[O:20])[C:9]([I:18])=[C:10]([NH:13][CH2:14][C:15](=[O:17])[CH3:16])[C:11]=1[I:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 145334-Aminophenylacetic acidHCID 21715954HCID 21715954, compound

Product 1

HCID 86755325HCID 86755325, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of MDTA-Cl X (2.18 g, 3.3 mmole) and p-aminophenylacetic acid (1.2 g, 8.27 mmole) in DMA (8 mL) was stirred at 60° C. for 30 h. The solvent was removed and the residue was treated with hot EtOAc (600 mL) containing EtOH (25 mL). The solution was filtered and the filtrate was freed of the solvent. The solid was recrystallized from EtOAc--EtOH to afford the title compound as a white amorphous solid (1.54 g, 57%).

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with hot EtOAc (600 mL)
  3. additioncontaining EtOH (25 mL)
  4. filtrationThe solution was filtered
  5. customThe solid was recrystallized from EtOAc

Sources & evidence

ORD record
ord-4b9c6eb13a524124aadce41ecaad11cf
Source dataset
uspto-grants-2000_04
Patent number
US06051210

Reaction notes

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