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

HRID 85139

Reaction equation

HRID 85139 reaction equation
[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]>CCO.[Pd]>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:11]=[C:2]([NH2:1])[C:3]=1[NH2:18]

Participants

4

Reactant 1

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

Product 1

HCID 58279190Methyl 2,3-diamino-5-morpholinobenzoateYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 3-amino-5-morpholino-2-nitrobenzoate (72; 2.1 g, 7.5 mmol) in EtOH (100 ml) was hydrogenated over 5% Pd/C (200 mg) at room temperature. After 3 h, the reaction mixture was filtered and concentrated under reduced pressure to afford 2,3-diamino-5-morpholin-4-yl-benzoic acid methyl ester 73 (1.3 g, 69.5%) as a brown yellow solid.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0f44400149b41d28949fd764b92d053
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

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