Hydrochloric Acid → 2-(3-Methoxy-4-nitrophenyl)ethylamine

HRID 1032529

Reaction equation

HRID 1032529 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O.Cl.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13][NH2:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 136293172-(3-Methoxy-4-nitrophenyl)acetonitrile

Product 1

HCID 221660082-(3-Methoxy-4-nitrophenyl)ethylamineYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice cooling, 17.0 g of 2-(3-methoxy-4-nitrophenyl)acetonitrile in 50 ml of tetrahydrofuran is combined with 180 ml of 1-molar borane-tetrahydrofuran complex in tetrahydrofuran, stirred for 16 hours at room temperature, and mixed with water. The mixture is agitated at 0° C. for 0.5 hour, 200 ml of 2N hydrochloric acid is added dropwise, and the mixture is again stirred for 2 hours at 0° C. and for 2 hours at room temperature. A pH of 9.5°-10.5 is set with sodium hydroxide solution, and the mixture is extracted four times with ethyl acetate/butanol 10:1. The product is chromatographed on silica gel with methanol/dichloromethane 1:1, thus obtaining 9.0 g of 2-(3-methoxy-4-nitrophenyl)ethylamine as an oil.

Workup

  1. stirringThe mixture is agitated at 0° C. for 0.5 hour
  2. stirringthe mixture is again stirred for 2 hours at 0° C. and for 2 hours at room temperature
  3. extractionthe mixture is extracted four times with ethyl acetate/butanol 10:1
  4. customThe product is chromatographed on silica gel with methanol/dichloromethane 1:1

Sources & evidence

ORD record
ord-ca0a99e3ad7e4f83968e539d128b497e
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Linked notes

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