Nitric Acid → 4-[(2-Aminoethyl)amino]-4-oxobutan-2-yl nitrate

HRID 1607125Notes

Reaction equation

HRID 1607125 reaction equation
[OH:1][CH:2]([CH3:10])[CH2:3][C:4]([NH:6][CH2:7][CH2:8][NH2:9])=[O:5].[N+:11]([O-])([OH:13])=[O:12]>C(OCC)C>[O:1]([CH:2]([CH3:10])[CH2:3][C:4]([NH:6][CH2:7][CH2:8][NH2:9])=[O:5])[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 13715405HCID 13715405, compound

Product 1

HCID 137153344-[(2-Aminoethyl)amino]-4-oxobutan-2-yl nitrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

30 g. 2-(3-Hydroxybutanoylamino)-ethylamine are slowly introduced, with stirring at 5° to 10° C., into 100% nitric acid. After stirring for 2 hours at 0° to 5° C., the reaction solution is stirred into 1 liter of ice-cooled anhydrous diethyl ether, the supernatant ethereal layer is decanted off, the separated oil is covered with methylene chloride and the base is liberated with sodium carbonate. After suction filtration and evaporation in a vacuum at a maximum bath temperature of 20° C., there are obtained 33 g. (84% of theory) of base in the form of an oil.

Workup

  1. customthe supernatant ethereal layer is decanted off
  2. filtrationAfter suction filtration and evaporation in a vacuum at a maximum bath temperature of 20° C., there
  3. customare obtained 33 g

Sources & evidence

ORD record
ord-164b2e6913224446aa13747c5396098b
Source dataset
uspto-grants-1989_09
Patent number
US04863949

Reaction notes

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