Hydrazine hydrate (1:1) → HCID 59441998, compound

HRID 1014279Notes

Reaction equation

HRID 1014279 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([N+:16]([O-])=O)[CH:14]=2)[CH2:9][CH2:8]1)=[O:6].O.NN>CO.[Fe](Cl)(Cl)Cl>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59442105HCID 59442105, compound

Product 1

HCID 59441998HCID 59441998, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
64 °C

Procedure

To N,N-dimethyl-3[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-3-oxo-1-propanamine (1.52 g, 5.4 mmol) in MeOH (50 mL) was added iron (III) chloride (0.220 g, 1.35 mmol, Aldrich) and activated carbon (2.0 g, Aldrich). The reaction mixture was stirred at 64° C. for 20 min before the dropwise addition of hydrazine hydrate (1.2 mL, 37.5 mmol, Aldrich) over 5 min. The reaction was kept stirring at 64° C. for additional 12 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 1-[3-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (0.270 g, 19% Yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.72 (s, 1 H), 6.63 (s, 1 H), 3.95-4.15 (m, 2 H), 3.81 (s, 3 H), 3.76 (s, 2 H), 3.10 (t, J=8.43 Hz, 2 H), 2.83-2.96 (m, 2 H), 2.70 (t, J=7.15 Hz, 2 H), 2.41 (s, 6 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-c231e2ca5d7343299bba0e1af7f3f8be
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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