Hydrochloric Acid → 2,5-Dimethoxy-4-nitrophenethylamine

HRID 565183Notes

Reaction equation

HRID 565183 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[CH2:5][CH2:6][NH2:7].Cl.[N+:15]([O-])([OH:17])=[O:16].[OH-].[Na+]>O>[N+:15]([C:10]1[C:9]([O:12][CH3:13])=[CH:8][C:4]([CH2:5][CH2:6][NH2:7])=[C:3]([O:2][CH3:1])[CH:11]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 944Nitric Acid3×HCID 14798Sodium HydroxideHCID 766322,5-Dimethoxyphenethylamine

Product 1

HCID 100366372,5-Dimethoxy-4-nitrophenethylamineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

45.5 g (250 mmol) 2,5-dimethoxyphenethylamine J1 was mixed with 40 ml water and cooled to 0° C. while 30 ml conc. HCl was added slowly. The resultant milky emulsion was cooled to 0 to 5° C., and 65 ml conc. HNO3 was added slowly and carefully within about 2 hours, keeping the temperature 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, was basified with 40% NaOH to pH>12 and then extracted with 2×11 CHCl3. The CHCl3 extraction was back washed with 3×110.5 M NaOH and dried over 15 g K2CO3. The solvent was evaporated to afford 49.8 g orange oil (yield: 88%), which crystallized when cooled.

Workup

  1. additionwas added slowly
  2. customthe temperature below 10° C
  3. additionhad been added
  4. temperatureThe mixture was warmed up to room temperature
  5. extractionextracted with 2×11 CHCl3
  6. extractionThe CHCl3 extraction
  7. washwas back washed with 3×110.5 M NaOH
  8. dry with materialdried over 15 g K2CO3
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b3a51873e72e4e26be6e39b20363e307
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

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