N1,N1,N2-Trimethyl-N2-(6-nitropyridin-3-yl)ethane-1,2-diamine → N5-(2-(Dimethylamino)ethyl)-N5-methylpyridine-2,5-diamine

HRID 1919076Notes

Reaction equation

HRID 1919076 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:7]=[N:8][C:9]([N+:12]([O-])=O)=[CH:10][CH:11]=1>C(O)C>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[N:8][CH:7]=1

Participants

3

Reactant 1

HCID 58043905N1,N1,N2-Trimethyl-N2-(6-nitropyridin-3-yl)ethane-1,2-diamine

Product 1

HCID 58043814N5-(2-(Dimethylamino)ethyl)-N5-methylpyridine-2,5-diamineYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 1.00 g dry weight) and a solution of 270a (2.20 g, 9.80 mmol) in ethanol (150 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 3 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (1.00 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a quantitative yield of 270b (1.91 g) as a purple oil: 1H NMR (500 MHz, CDCl3) d 7.67 (d, 1H, J=2.9 Hz), 7.05 (dd, 1H, J=8.5, 2.9 Hz), 6.48 (dd, 1H, J=8.9, 0.5 Hz), 4.04 (br s, 2H), 3.28 (t, 2H, J=7.1 Hz), 2.84 (s, 3H), 2.43 (t, 2H, J=7.4 Hz), 2.26 (s, 6H); MS (ESI+) m/z 195.2 (M+H).

Workup

  1. customA 250-mL Parr reactor bottle was purged with nitrogen
  2. additioncharged with 10% palladium on carbon (50% wet, 1.00 g dry weight)
  3. customevacuated
  4. additioncharged with hydrogen gas to a pressure of 50 psi
  5. customAfter this time, the hydrogen was evacuated
  6. additionnitrogen was charged into the bottle
  7. additionCelite 521 (1.00 g) was added
  8. filtrationthe mixture was filtered through a pad of Celite 521
  9. washThe filter cake was washed with ethanol (2×25 mL)
  10. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-567af7973caf4ef78e2f1236d46efe79
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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