(4-Nitrophenyl)acetic acid → HCID 21939891, compound

HRID 1242949Notes

Reaction equation

HRID 1242949 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:10])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.[N+:47]([C:50]1[CH:55]=[CH:54][C:53]([CH2:56][C:57](O)=[O:58])=[CH:52][CH:51]=1)([O-:49])=[O:48]>C(OCC)(=O)C.O.CN(C=O)C>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][NH:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:57](=[O:58])[CH2:56][C:53]2[CH:52]=[CH:51][C:50]([N+:47]([O-:49])=[O:48])=[CH:55][CH:54]=2)=[CH:7][CH:6]=1

Participants

9

Reactant 5

HCID 4661(4-Nitrophenyl)acetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 10704226HCID 10704226, compound

Product 1

HCID 21939891HCID 21939891, compoundYield 20.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide (221 mg), WSC (free form: 0.23 ml), 1-hydroxybenzotriazole (199 mg), and dimethylaminopyridine (244 mg) were added to a DMF (5 ml) solution of 4-nitrophenylacetic acid (181 mg), which was stirred for 4 hours. The reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated. The residue was recrystallized from methanol, to give the titled compound (80 mg).

Workup

  1. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-faeac1878a8246a6aeecc593b773a528
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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