Triethylamine → Methyl 4-(3-(1-acetylpiperazin-4-yl)anilino)-3-nitrobenzoate

HRID 324738

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=2)[NH2:27])[CH2:20][CH2:19]1)(=[O:17])[CH3:16].C(N(CC)CC)C>CN1C(=O)CCC1>[C:15]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=2)[NH:27][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:22][CH2:23]1)(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 4-chloro-3-nitrobenzoate (2.0 g, 9.28 mmol) in anhydrous NMP (5 ml) was added 2d (2.03 g, 9.28 mmol) and triethylamine (1.3 ml, 9.28 mmol). The mixture was heated with stirring to 80° C. overnight. The cooled solution was poured into ice-water (50 ml) and the resulting mixture was extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with water, dried over sodium sulfate and evaporated to dryness. The residue was triturated with petroleum ether to yield methyl 4-(3-(1-acetylpiperazin-4-yl)anilino)-3-nitrobenzoate (3.14 g, 85%) as red crystals.

Workup

temperatureThe mixture was heated
extractionthe resulting mixture was extracted with ethyl acetate (3×10 ml)
washThe combined organic extracts were washed with water
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe residue was triturated with petroleum ether

Sources & evidence

ORD record: ord-33d64f71547541ccbe2ea65f43ebf04b
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218547B1

Linked notes

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