4-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acid → 3-Amino-4-(2-methylpiperidin-1-yl)benzoic acid

HRID 219818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219818
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[N+:17]([O-])=O.[H][H]>[Pd]>[NH2:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[CH3:1])[C:12]([OH:14])=[O:13]

Komponenten

4

Edukt 2

HCID 431767024-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 548890513-Amino-4-(2-methylpiperidin-1-yl)benzoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A methanolic solution of 4-(2-methylpiperidin-1-yl)-3-nitrobenzoic acid obtained in step 1 (500 mg; 1.89 mmol; 0.01 M) was pumped through an H-Cube (1 mL/min) fitted with a 10 mol % Pd/C catalyst cartridge (30×4 mm) and heated to 25° C. with the full hydrogen option enabled. Solvent was evaporated under vacuum to give the title compound as a pinkish oil (443 mg, 99%). 1H NMR (DMSO-d6, 300 MHz) δ 12.39 (bs, 1H), 7.28 (d, J=1.86 Hz, 1H), 7.14 (dd, J=8.1, 2.1 Hz, 1H), 6.99 (d, J=8.1 Hz, 1H), 5.01 (bs, 1H), 3.07-3.03 (m, 1H), 2.91-2.88 (m, 1H), 2.43-2.35 (m, 1H), 1.79-1.70 (m, 2H), 1.62-1.61 (m, 2H), 1.41-1.31 (m, 2H), 0.79 (d, J=6 Hz, 3H). HPLC (Method A) Rt 1.66 min (Purity: 99.2%).

Aufarbeitung

  1. customSolvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-666a063a4dd44216865f1e5e8e97987c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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