(4-Nitrophenyl)acetic acid → HCID 2726119, compound

HRID 890618Notes

Reaction equation

HRID 890618 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=1)([O-:12])=[O:11].Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:20](=[O:21])[CH2:19][C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 7732P-AnisidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2726119HCID 2726119, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of p-anisidine (4.92 g, 40 mmol), 4-nitrophenylacetic acid (7.25 g, 40 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (11.5 g, 60 mmol) in pyridine (40 mL) was stirred at room temperature overnight. The solvent was evaporated, and HCl (1M, 50 mL) was added. The resulting product was filtered and washed with water and ether, and recrystallized from ethanol to give N-(4-Methoxyphenyl)-2-(4-nitro-phenyl)-acetamide (9.6 g, 84%).

Workup

  1. customThe solvent was evaporated
  2. additionHCl (1M, 50 mL) was added
  3. filtrationThe resulting product was filtered
  4. washwashed with water and ether
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-06f6cae70f174c6aba27cc3bee7c5896
Source dataset
uspto-grants-2006_02
Patent number
US06998414B2

Reaction notes

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