Dimethyl Sulfate → 5-Nitro-3-(2-nitropropyl)indole

HRID 1381552Notes

Reaction equation

HRID 1381552 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].CN([CH2:9][C:10]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][CH:11]=1)C.COS(OC)(=O)=O>CCO>[N+:19]([C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][CH:17]=1)[NH:12][CH:11]=[C:10]2[CH2:9][CH:4]([N+:1]([O-:3])=[O:2])[CH3:5])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 6587NitroethaneHCID 18882Indole, 3-((dimethylamino)methyl)-5-nitro-

Product 1

HCID 143911385-Nitro-3-(2-nitropropyl)indoleYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 0.3 g (0.013 mole) of Na in 65 ml of abs EtOH was added 2.93 g (0.039 mole) of nitroethane dropwise. To the white suspension was added 2.19 g (0.01 mole) of 5-nitrogramine suspended in 40 ml of abs EtOH, followed by 2.5 g (0.02 mole) of dimethylsulfate in 20 ml of abs EtOH dropwise over 15 minutes. The mixture was stirred for 2 hours, then poured into 350 ml of ice water. The yellow solid was filtered, washed with ice water and air-dried to give 1.63 g (64%) of product: m.p. 130-131.5.

Workup

  1. filtrationThe yellow solid was filtered
  2. washwashed with ice water
  3. customair-dried

Sources & evidence

ORD record
ord-052a86b0a8584eb6b85557a08215150d
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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