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

HRID 539226Notes

Reaction equation

HRID 539226 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-2b9d50ec9457498cbde230ced30dc7e8
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Reaction notes

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