HCID 22181365, compound → HCID 69850017, compound

HRID 1796523Notes

Reaction equation

HRID 1796523 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[CH:8][N:7]=2)[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([NH2:12])=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[CH:8][N:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 22181365HCID 22181365, compound

Product 1

HCID 69850017HCID 69850017, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(cyclopropylmethyl)-3,5-dinitro-2-pyridinamine (1.17 g, 4.92 mmol) in EtOAc (50 mL) at room temperature was added Pd/C (394 mg, 0.25 mmol, 10% grade). The mixture was placed in a Parr apparatus under 35 psi H2. The mixture was shaken overnight. The reaction was filtered over Celite and concentrated in vacuo. The residue was purified using silica gel flash chromatography ([2.5% MeOH+1% NH4OH aq] in CH2Cl2) to provide 792 mg of the title compound N2-(cyclopropylmethyl)-5-nitro-2,3-pyridinediamine (77.3% yield from N-(cyclopropylmethyl)-3,5-dinitro-2-pyridinamine). 1H-NMR (400 MHz, CDCl3): δ 0.31 (m, 2H), 0.61 (m, 2H), 1.14 (m, 1H), 3.34 (br s, 2H), 3.42 (dd, J=5.3, 7.2 Hz, 2H), 5.15 (br s, 1H), 7.62 (d, J=2.5 Hz, 1H), 8.73 (d, J=2.5 Hz, 2H). MS (ESI) (M+H)+: 209.

Workup

  1. filtrationThe reaction was filtered over Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified

Sources & evidence

ORD record
ord-8846bef1c85247509f5e856dd3e97fbd
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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