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

HRID 49820

반응식

HRID 49820 반응식
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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 111175391-[4-(3-Aminophenyl)piperazin-1-yl]ethan-1-one

생성물 1

HCID 22741905Methyl 4-(3-(1-acetylpiperazin-4-yl)anilino)-3-nitrobenzoate수율 85%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d28c7b02f5b34d5cb4e0639f13bf4dc5
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710044B2

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