4-Aminophenylacetic acid → HCID 86755325, compound

HRID 1385804Notes

Reaction equation

HRID 1385804 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-EtOH

Sources & evidence

ORD record
ord-f2b7c60d1a204fc188cdff1fe927c7e3
Source dataset
uspto-grants-2001_07
Patent number
US06264916B1

Reaction notes

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