Nitric Acid → HCID 21075976, compound

HRID 1374057Notes

Reaction equation

HRID 1374057 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[N+:6]([O-:9])([OH:8])=[O:7].CC(OC(C)=O)=O>CCOC(C)=O.CCCCCC>[N+:6]([O-:9])([O-:8])=[O:7].[CH3:1][NH2+:2][CH2:3][CH2:4][O:5][N+:6]([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 80162-(Methylamino)ethanol

Product 1

HCID 21075976HCID 21075976, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-10 °C

Procedure

Methyl(2-(hydroxy)ethyl)amine (1.5 g, 20 mmol) in EtOAc (65 mL) was added dropwise to a mixture of fuming HNO3 (6.3 g, 4.2 mL, 100 mmol) and Ac2O (16.3 g, 15.1 mL, 160 mmol) at −10° C. The reaction mixture was stirred at −10° C. for 30 minutes and diluted with EtOAc and hexane. The precipitate was collected by filtration and washed with hexane to give the title compound (2.79 g, 82% yield) as an off-white solid. Mp 58–62° C. 1H NMR (300 MHz, d6-DMSO) δ 4.59–4.67 (m, 2H), 4.64–4.73 (m, 2H), 2.61 (bs, 3H). 13C NMR (75 MHz, d6-DMSO) δ 59.8, 38.7, 24.4. Mass spectrum (API-TIS) m/z 121 (MH+).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-6593250e126e4d0098c42fee055e7f34
Source dataset
uspto-grants-2007_01
Patent number
US07163958B2

Reaction notes

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