Nitric Acid → HCID 21075974, compound

HRID 1514769Notes

Reaction equation

HRID 1514769 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][OH:6])[CH3:2].[N+:7]([O-:10])([OH:9])=[O:8].CC(OC(C)=O)=O>CCOC(C)=O.CCCCCC>[N+:7]([O-:10])([O-:9])=[O:8].[CH2:1]([NH2+:3][CH2:4][CH2:5][O:6][N+:7]([O-:9])=[O:8])[CH3:2]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 80722-(Ethylamino)ethanol

Product 1

HCID 21075974HCID 21075974, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-10 °C

Procedure

Ethyl(2-(hydroxy)ethyl)amine (5 g, 56 mmol) in EtOAc (60 mL) was added drop-wise to a mixture of fuming HNO3 (17.7 g, 11.8 mL, 280 mmol) and Ac2O (45.8 g, 42.3 mL, 448 mmol) at −10° C. The reaction mixture was stirred at −10° C. for 30 minutes and diluted with EtOAc and hexane. The oil layer was separated and dried in high vacuo to give the title compound (8.4 g, 76% yield) as a pale green oil. 1H NMR (300 MHz, d6-DMSO) δ 8.60-8.95 (bs, 2H), 4.84 (m, 2H), 3.37-3.49 (m, 2H), 3.02-3.16 (m, 2H), 1.24 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) δ 69.1, 43.6, 42.6, 11.0. Mass spectrum (API-TIS) m/z 135 (MH+).

Workup

  1. customThe oil layer was separated
  2. customdried in high vacuo

Sources & evidence

ORD record
ord-60f3f6122a0c45e59a434cae41360c0c
Source dataset
uspto-grants-2012_07
Patent number
US08222277B2

Reaction notes

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