Ammonia → HCID 22611536, compound

HRID 1186270Notes

Reaction equation

HRID 1186270 reaction equation
[CH2:1]([N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=3)[NH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].O.NN.N.C(Cl)Cl>CO.[Ni]>[CH2:1]([N:3]1[CH2:4][CH:5]=[C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 57474453HCID 57474453, compound

Product 1

HCID 22611536HCID 22611536, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole (0.375 g, 1.382 mmol) in dry methanol (10 mL) was treated with Raney-nickel (0.1 g, 0.351 mmol), followed by hydrazine hydrate (0.672 mL, 13.82 mmol) at room temperature. The resulting mixture was placed in a pre-heated oil bath and refluxed for 5 min. (TLC basis, 2 M NH3 in MeOH:CH2Cl2, 5:95). The reaction was brought to room temperature, filtered through celite bed and washed with methanol (3×5 mL). The combined methanol layer was evaporated and crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-amine (0.33 g, 99%) as a foam. 1H NMR (DMSO-d6) δ 10.60 (s, 1H), 7.15 (d, 1H, J=2.7 Hz), 7.05 (d, 1H, J=8.4 Hz), 7.00 (d, 1H, J=1.5 Hz), 6.48 (dd, 1H, J=2.1, 8.5 Hz), 5.98 (s, 1H), 4.48 (s, 2H), 3.10-3.04 (m, 2H), 2.59 (t, 2H, J=5.4 Hz), 2.54-2.39 (m, 4H, merged with DMSO peak), 1.06 (t, 3H, J=7.2 Hz); EI-MS (m/z, %): 241 (M+, 100).

Workup

  1. customThe resulting mixture was placed in a pre-heated oil bath
  2. customwas brought to room temperature
  3. filtrationfiltered through celite bed
  4. washwashed with methanol (3×5 mL)
  5. customThe combined methanol layer was evaporated
  6. customcrude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-42620a58d4bc4adf91422d29329dc561
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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