Hydrochloric Acid → HCID 21267689, compound

HRID 565186Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][C:5]=1[CH2:6][CH2:7][NH2:8])[CH3:2].Cl.[N+:17]([O-])([OH:19])=[O:18].[OH-].[Na+]>O>[N+:17]([C:11]1[C:10]([O:13][CH2:14][CH3:15])=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 2.5 °C

Procedure

5.23 g (25 mmol) 2,5-diethoxyphenethylamine N5 was mixed with 10 ml water and cooled to 0° C. while 3 ml conc. HCl was added slowly. The resultant milky emulsion was to cooled 0 to 5° C. and 13.5 ml conc. HNO3 was added slowly and carefully within about 2 hours. The temperature was kept below 10° C. The mixture solidified when about half of the HNO3 had been added. 50 ml icy water was added to render the mixture stirrable. Then the rest of the HNO3 was added. The mixture was warmed up to room temperature and stirred at room temperature for 3 hours, basified to pH>12 with 40% NaOH and then extracted with 2×100 ml CHCl3. The CHCl3 extraction was back washed with 3×100 ml 0.5 M NaOH and dried over 10 g K2CO3. The solvent was evaporated to afford 3.22 g orange oil (yield: 52%), which crystallized when cool.

Workup

additionwas added slowly
customwas kept below 10° C
additionhad been added
temperatureThe mixture was warmed up to room temperature
extractionextracted with 2×100 ml CHCl3
extractionThe CHCl3 extraction
washwas back washed with 3×100 ml 0.5 M NaOH
dry with materialdried over 10 g K2CO3
customThe solvent was evaporated

Sources & evidence

ORD record: ord-32363d4aab3841c1819e87ece45eec0b
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06171866B2

Reaction notes

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