Hydrazine → Aminotetrahydrocyclopenta[b]indole

HRID 1928574Notes

Reaction equation

HRID 1928574 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). Preferred conditions use tetrahydrofuran/ethanol in a mixture of about 20/1 by volume at a temperature of about 40 to 70° C., for 1 to 12 hours. The resulting phthalhydrazide is removed by filtration and the product isolated by concentration of the filtrate.

Sources & evidence

ORD record
ord-4622333723e94532b7c4b1cf90d82dd1
Source dataset
uspto-grants-2012_05
Patent number
US08183388B2

Reaction notes

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