Hydrazine → Aminotetrahydrocyclopenta[b]indole

HRID 449822Notes

Reaction equation

HRID 449822 reaction equation
[CH2:1]1[C:12]2[CH:4]([N:5]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[NH2:13]N.O.NN>>[NH2:13][CH:1]1[C:12]2[CH:4]([N:5]=[C:6]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 66869719Tetrahydrocyclopent(b)indole

Product 1

HCID 66933239Aminotetrahydrocyclopenta[b]indole

Procedure

In Scheme 1, Step C, the phthalimide group of the tetrahydrocyclopenta[b]indole of formula (2) is cleaved with hydrazine or hydrazine hydrate to provide an aminotetrahydrocyclopenta[b]indole of formula (3) using conditions as described by M. Alajarín, et al (Eur. J. Org. Chem. 2002, 4222-4227). The reaction proceeds in a solvent mixture of tetrahydrofuran/ethanol in a ratio of about 5.5/1 by volume at a temperature of 0 to 50° C., preferably at about room temperature, for 4 to 72 hours. The resulting phthalhydrazide is removed by filtration and the product isolated by concentration of the filtrate. It may be purified by chromatography using techniques known in the art.

Sources & evidence

ORD record
ord-56fd0fffbc0e42cdb78077eb6db47747
Source dataset
uspto-grants-2013_07
Patent number
US08486943B2

Reaction notes

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