Methyl 3-amino-5-morpholino-2-nitrobenzoate → Methyl 2,3-diamino-5-morpholinobenzoate

HRID 44547

Reaktionsgleichung

Reaktionsgleichung von HRID 44547
[NH2:1][C:2]1[C:3]([N+:18]([O-])=O)=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]>CO.[Pd]>[NH2:18][C:3]1[C:2]([NH2:1])=[CH:11][C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Komponenten

4

Edukt 1

HCID 58278827Methyl 3-amino-5-morpholino-2-nitrobenzoate

Produkt 1

HCID 58279190Methyl 2,3-diamino-5-morpholinobenzoateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of intermediate methyl 3-amino-5-(4-morpholinyl)-2-nitrobenzoate, prepared as described in Example 26, step c (98 g, 0.35 mol) in MeOH (2.2 L) was added Pd/C (9.8 g, 10%) and the resulting mixture was then stirred at room temperature under H2 (4 atm) atmosphere. After stirring for 16 h, it was filtered and concentrated in vacuum to give the crude product (84.4 g, 96%) as a dark solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.85 (t, 4H, J=4.8 Hz), 3.70 (t, 4H, J=4.8 Hz), 3.76 (s, 3H), 4.77 (br. S, 2H), 5.86 (br. S, 2H), 6.54 (d, 1H, J=2.7 Hz), 6.61 (d, 1H, J=2.7 Hz); LC-MS: m/e=252 [M+1]+

Aufarbeitung

  1. customprepared
  2. stirringAfter stirring for 16 h
  3. filtrationit was filtered
  4. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fc70c6c15bed4cb2aff8bac6362b1dab
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541411B2

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