Oxalic Acid → 3-Nitro-phenethylamine oxalate

HRID 1358472Notes

Reaction equation

HRID 1358472 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13]([OH:18])(=[O:17])[C:14]([OH:16])=[O:15]>C1COCC1>[C:13]([OH:18])(=[O:17])[C:14]([OH:16])=[O:15].[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][CH2:11][NH2:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 121253-Nitrophenylacetonitrile

Product 1

HCID 181845273-Nitro-phenethylamine oxalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Nitrophenyl acetonitrile (6.486 g, 0.04 mol) was refluxed with borane-THF complex (40 mL, 0.04 mole) in anhydrous THF (80 mL) for 45 min under argon. The reaction mixture was quenched with methanol and concentrated. 3-Nitrophenylethyl amine was crystallized from the reaction mixture by adding oxalic acid (10 g, 0.08 mol). Yield 4.36 g, 85%.

Workup

  1. customThe reaction mixture was quenched with methanol
  2. concentrationconcentrated
  3. custom3-Nitrophenylethyl amine was crystallized from the reaction mixture

Sources & evidence

ORD record
ord-bd137f1d77d04b8889d7f0779a4293bb
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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