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Hydrazine hydrate (1:1) → HCID 57701032, compound

HRID 1186285
Notes
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Reaction equation

HRID 1186285 reaction equation
[CH2:1]([N:3]([CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:26]([O-])=O)[CH:24]=3)[NH:19][CH:18]=2)[CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].O.NN>CO.O.[Ni]>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:13]1[CH2:14][CH2:15][CH2:16][CH:11]([N:3]([CH2:1][CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57701041HCID 57701041, compound

Product 1

HCID 57701032HCID 57701032, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962
Water
Solvent

Procedure

To a solution of tert-butyl ethyl(3-(5-nitro-1H-indol-3-yl)cyclohexyl)carbamate (0.24 g, 0.62 mmol) in dry MeOH (10 mL) was added Raney-Ni (0.1 g as a slurry in water) and hydrazine hydrate (0.30 mL, 6.20 mmol). The resulting mixture was immersed in a preheated oil bath and refluxed for 15 min. or until the solution became clear. The reaction was cooled and filtered trough celite, washed with MeOH (20 mL) and the solvent evaporated. The crude material was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98) to give the title compound as a brownish solid (0.21 g, 96%). 1H-NMR (CDCl3) δ1.09 (t, 3H, J=6.9 Hz), 1.30-1.66 (m, 3H), 1.48 (s, 9H), 1.80-1.83 (m, 1H), 1.90-1.94 (m, 1H), 1.98-2.04 (m, 1H), 2.11-2.15 (m, 1H), 2.80-2.90 (m, 1H), 3.05-3.22 (m, 2H), 4.12-4.19 (m, 1H), 6.65 (dd, 1H, J=2.1, 8.7 Hz), 6.87 (d, 1H, J=2.1 Hz), 6.96 (s, 1H), 7.15 (d, 1H, J=8.7 Hz), 7.725 (s, 1H); EI-MS (m/z, %) 357 (M+, 100).

Workup

  1. customThe resulting mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 15 min. or until the solution
  3. temperatureThe reaction was cooled
  4. filtrationfiltered trough celite
  5. washwashed with MeOH (20 mL)
  6. customthe solvent evaporated
  7. customThe crude material was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98)

Sources & evidence

ORD record
ord-37c600d74f2f44818bc05e45ceaf790a
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673909B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes