2-Nitrobutane → 3-(2'-Methyl-2'-aminopentyl)-indole

HRID 268463Notes

Reaction equation

[N+](C(CC)C)([O-])=O.[N+](C(CCC)C)([O-])=O.[CH3:16][C:17]([N+:31]([O-])=O)([CH2:28][CH2:29][CH3:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1>>[CH3:16][C:17]([NH2:31])([CH2:28][CH2:29][CH3:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1

Participants

Reactant 3

HCID 117492-Nitrobutane

HCID 1457562-Nitropentane

HCID 215522303-(2'-Methyl-2'-nitropentyl)-indole

Product 1

HCID 215522493-(2'-Methyl-2'-aminopentyl)-indole

Procedure

If the 2-nitrobutane in Example 1 is replaced by the corresponding quantity of 2-nitropentane, using the same procedure as in Example 1, the intermediate product obtained is 3-(2'-methyl-2'-nitropentyl)-indole; melting point 78°-80°C (from petroleum ether). Reduction yielded 3-(2'-methyl-2'-aminopentyl)-indole, which after recrystallisation from petroleum ether yields needle-shaped crystals of a melting point of 73.5° to 74.5°C.

Workup

customthe intermediate product obtained

Sources & evidence

ORD record: ord-4380c599b30e4fd589d8d50ad317959a
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947584

Reaction notes

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