Phenethylamine → HCID 4262649, compound

HRID 2186055Notes

Reaction equation

HRID 2186055 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[CH2:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[C:17]1([CH2:16][CH2:15][N:23]2[C:11](=[O:12])[C:6]3=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=[C:7]3[C:8]2=[O:10])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 4262649HCID 4262649, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-nitrophthalic anhydride (18 g, 93.3 mmol) and phenethylamine (11.5 g, 95 mmol) in toluene (250 mL) was heated to reflux using a Dean-Stark trap to remove water. After 2.5 h, the mixture was concentrated to solid residue, which was triturated and filtered to give the titled compound (24.5 g, 89%): mp 142-3° C.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customto remove water
  4. concentrationthe mixture was concentrated to solid residue, which
  5. customwas triturated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f92c8e8b56124a1a97d4f545891148f3
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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