2,3-Dimethyl-4-methoxyphenylacetonitrile → 4-Methoxy-2,3-dimethylbenzeneethanamine

HRID 6728Notes

Reaction equation

HRID 6728 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[C:5]([CH3:12])[C:4]=1[CH3:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[C:5]([CH3:12])[C:4]=1[CH3:13]

Participants

4

Reactant 2

HCID 5948942,3-Dimethyl-4-methoxyphenylacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 106789204-Methoxy-2,3-dimethylbenzeneethanamineYield 63.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (4-methoxy-2,3-dimethylphenyl)acetonitrile (0.20 g) in 15 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.20 g) was added in portions to the stirring nitrile solution. The resulting slurry was allowed to warm to rt and stirred for 20 h. The mixture was cooled to 0° C. and carefully quenched by the sequential addition of 0.2 mL of water, followed by 0.2 mL of 3 N sodium hydroxide and 0.6 mL of water. The mixture was stirred for 15 min and filtered to remove the aluminum salts. The filtrate was collected and the volatile material was removed by a rotary evaporator to give 130 mg of 2-(4-methoxy-2,3-dimethylphenyl)ethylamine.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customcarefully quenched by the sequential addition of 0.2 mL of water
  3. stirringThe mixture was stirred for 15 min
  4. filtrationfiltered
  5. customto remove the aluminum salts
  6. customThe filtrate was collected
  7. customthe volatile material was removed by a rotary evaporator

Sources & evidence

ORD record
ord-daef2d8ef2434000bcefaa426439a026
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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