Hydrazine hydrate (1:1) → 7-(Benzyloxy)-1H-indole

HRID 1193485Notes

Reaction equation

HRID 1193485 reaction equation
O.NN.[N+]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][C:8]=1[CH:21]=[CH:22][N:23]1CCCC1)([O-])=O>CO.[Ni]>[CH2:14]([O:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[NH:23][CH:22]=[CH:21]2)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 53800756HCID 53800756, compound2×

Product 1

HCID 2607987-(Benzyloxy)-1H-indole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrazine hydrate (4.6 g, 92 mmol, 85% solution) was added to a mechanically stirred mixture of 1-[2-[2-nitro-3-(phenylmethoxy)phenyl]ethenyl]pyrrolidine and N-methyl-N-[2-[2-nitro-3-(phenylmethoxy)phenyl]ethenyl]methanamine (20 g, 61.8 mmol, crude product obtained as described in Step 2) and Raney-Nickel (5 g) in methanol (500 mL), care being taken to keep the temperature at 45°-50° C. Two additional portions of hydrazine hydrate (4.6 g each ) were added after 30 and 60 minutes, respectively. The temperature was maintained at 45°-50° C. for 5 hours. After stirring overnight at room temperature, the mixture was filtered off (Celite) and the filtrate was concentrated in vacuo. The residue (dark liquid) was purified by flash-chromatography (on silica Merck-60, dichloromethane-light petroleum ether 1:1) to yield pure 7-benzyloxyindole as an oil that solidifies upon standing (2.3-3.03 g, 17-22%, based upon different runs). A sample was recrystallized from petroleum ether as white needles, m.p. 62°-63° C. (Dictionary of Organic Compounds Vol III, p 3077, m.p. 67°-68° C., ligroin).

Workup

  1. customat 45°-50° C
  2. temperatureThe temperature was maintained at 45°-50° C. for 5 hours
  3. filtrationthe mixture was filtered off (Celite)
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue (dark liquid) was purified by flash-chromatography (on silica Merck-60, dichloromethane-light petroleum ether 1:1)

Sources & evidence

ORD record
ord-d8979a8fe2f84456adf3062b9d88c79b
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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