Methyl 2-amino-6-morpholino-3-nitroisonicotinate → Methyl 2,3-diamino-6-morpholinoisonicotinate

HRID 1399786Notes

Reaction equation

HRID 1399786 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)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]>CO.CC(O)=O.[Pd]>[NH2:1][C:2]1[C:3]([NH2:18])=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 1

HCID 89648265Methyl 2-amino-6-morpholino-3-nitroisonicotinate2×

Product 1

HCID 89647670Methyl 2,3-diamino-6-morpholinoisonicotinate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-amino-6-morpholino-3-nitroisonicotinate (4.8 g, 17 mmol) and 10% Pd/C (480 mg) in MeOH (100 mL) and CH3COOH (50 mL) was stirred at room temperature for 16 h with connection to a balloon of H2. LCMS showed no methyl 2-amino-6-morpholino-3-nitroisonicotinate left and the desired product formed. It was then filtered and the filtrate was concentrated in vacuo. The residue (4.3 g) was used for next step without purification. LC/MS: MS (ES+) m/e 253 (MH+).

Workup

  1. waitleft

Sources & evidence

ORD record
ord-ba6aa531829348b4840932597f3cbad7
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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