2-Methoxy-4-nitroaniline → N-(2-methoxy-4-nitrophenyl)-2-(1-pyrrolidinyl)acetamide

HRID 2384894

Reaktionsgleichung

Reaktionsgleichung von HRID 2384894
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH2:12].Cl.[N:14]1([CH2:19][C:20](O)=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:12][C:20](=[O:21])[CH2:19][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

7

Edukt 4

HCID 73372-Methoxy-4-nitroanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 130220162-(Pyrrolidin-1-yl)acetic acid hydrochloride

Produkt 1

HCID 2976819N-(2-methoxy-4-nitrophenyl)-2-(1-pyrrolidinyl)acetamideAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 2-methoxy-4-nitro-phenylamine (1.0 g, 5.95 mmol), pyrrolidin-1-yl-acetic acid hydrochloride (0.99 g, 5.95 mmol) and N,N-diisopropylethylamine (1.08 mL, 6.55 mmol) in N,N-dimethylformamide (20 mL) and add O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.49 g, 6.55 mmol). Stir the mixture at room temperature for 16 h. Dilute the mixture with water (50 mL) and extract with dichloromethane (3×25 mL). Dry the combined organics (Na2SO4), filter, and concentrate in vacuo. Purify by chromatography (0% to 4% MeOH/CH2Cl2) to afford 0.77 g (46%) of the title compound. MS/ES m/z 280.0 [M+H]+.

Aufarbeitung

  1. extractionextract with dichloromethane (3×25 mL)
  2. dry with materialDry the combined organics (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography (0% to 4% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-40255553842c4a15a7fc6f93d03c34c3
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263772B2

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