Phenethylamine → 4-Nitrophenethylamine

HRID 1681668Notes

Reaction equation

HRID 1681668 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[N+:15]([O-])([O-:17])=[O:16].[NH4+].[OH-].[NH4+]>>[N+:15]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][CH2:1][NH2:9])=[CH:4][CH:5]=1)([O-:17])=[O:16]

Participants

5

Reactant 4

HCID 1001PhenethylamineHCID 1118Sulfuric Acid2×HCID 14923Ammonium HydroxideHCID 22985Ammonium nitrate

Product 1

HCID 951534-Nitrophenethylamine

Procedure

24.2 g. (0.20 mol) Phenethylamine are carefully mixed in an ice-bath with 125 ml. concentrated sulphuric acid. After stirring for 1 hour, 16.8 g. (0.21 mol) ammonium nitrate in 125 ml. concentrated sulphuric acid are carefully added dropwise thereto at 0° to 5° C. After a further hour, the reaction mixture is poured on to 1.5 liters of ice and the pH adjusted to 9 with a concentrated aqueous solution of ammonium hydroxide. The aqueous phase is extracted several times with diethyl ether, the combined organic phases are dried over anhydrous magnesium sulphate, evaporated to dryness and the residue is distilled. There are obtained 14.5 g. (44% of theory) of a colourless oil; b.p. 110°-115° C./0.01 Torr. 1H-NMR (60 MHz, CDCl3, ppm): δ=2.99 (q, 2H, J=2.0 Hz, CH2); 3.05 (t, 2H, J=2.0 Hz, CH2).

Workup

  1. customat 0° to 5° C
  2. waitAfter a further hour
  3. extractionThe aqueous phase is extracted several times with diethyl ether
  4. dry with materialthe combined organic phases are dried over anhydrous magnesium sulphate
  5. customevaporated to dryness
  6. distillationthe residue is distilled
  7. customThere are obtained 14.5 g

Sources & evidence

ORD record
ord-7896acaa239a45c4b3d1293d45e27fd8
Source dataset
uspto-grants-1992_12
Patent number
US05173500

Reaction notes

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