Sulfuric Acid → HCID 22708335, compound

HRID 1956554Notes

Reaction equation

HRID 1956554 reaction equation
C(C1NC2C(C=1)=CC=CC=2)C.[N+]([O-])([O-])=O.[Na+].S(=O)(=O)(O)O.[N+:22]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([CH2:34][CH3:35])=[CH:28]2)([O-])=O.CC(C)CCC1NC2C(C=1)=CC=CC=2>>[NH2:22][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([CH2:34][CH3:35])=[CH:28]2

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 2803102-Ethyl-5-nitro-1H-indoleHCID 38016182-ethyl-1H-indoleHCID 11041488Isopentylindol

Product 1

HCID 22708335HCID 22708335, compound

Procedure

This synthesis could be achieved beginning with a standard nitration of 2-ethylindole using sodium nitrate and sulfuric acid similar to that cited in Yokoyama; Tanaka; Yamane; Kurita; Chem. Lett.; 7; 1991; 1125-1128. The resultant 5-nitro-2-ethylindole could be reduced to the desired amino compound using catalytic hydrogenation as in 28b).

Workup

  1. customThis synthesis

Sources & evidence

ORD record
ord-3aef9d8fa0394b50b1a99807dac5f6fe
Source dataset
uspto-grants-1998_07
Patent number
US05780496

Reaction notes

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