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

HRID 1188846Notes

Reaction equation

HRID 1188846 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]>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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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]+

Workup

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

Sources & evidence

ORD record
ord-00e855a5a0f040c988f2d1761d1e8351
Source dataset
uspto-grants-2014_03
Patent number
US08674090B2

Reaction notes

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