Hydrazine hydrate (1:1) → HCID 59442111, compound

HRID 1014175Notes

Reaction equation

HRID 1014175 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH2:16][N:15]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.O.NN>CO.[Fe](Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH2:16][N:15]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59441646HCID 59441646, compound

Product 1

HCID 59442111HCID 59442111, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
64 °C

Procedure

To 5-(3-methyl-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine (5.0 g, 19.2 mmol) in MeOH (100 mL) was added iron (III) chloride (0.93 g, 5.8 mmol, Aldrich) and activated carbon (1.0 g, Aldrich). The reaction mixture was stirred at 64° C. for 20 min before the dropwise addition of hydrazine hydrate (11.5 mL, 230.8 mmol, Aldrich) over 5 min. The reaction was kept stirring at 64° C. for additional 5 h. Filtration removed the solids and the filtrate was concentrated and purified via chromatography on SiO2 (0-10% 2 M NH3 in MeOH/DCM) to afford 2-methyl-4-(1-propyl-1,2,5,6-tetrahydro-3-pyridinyl)aniline (3.6 g, 82% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 0.94 (t, J=7.4 Hz, 3 H), 1.57-1.67 (m, 2 H), 2.16 (s, 3 H), 2.33 (tt, J=5.9, 2.9 Hz, 2 H), 2.44-2.50 (m, 2 H), 2.59 (t, J=5.8 Hz, 2 H), 3.29 (q, J=2.0 Hz, 2 H), 3.58 (s, 2 H), 5.96 (dq, J=3.9, 2.0 Hz, 1 H), 6.61 (d, J=7.9 Hz, 1 H), 7.02-7.06 (m, 2 H).

Workup

  1. filtrationFiltration
  2. customremoved the solids
  3. concentrationthe filtrate was concentrated
  4. custompurified via chromatography on SiO2 (0-10% 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-301a27e46a994670878b6f7789bc2a83
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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