4-amino-3,5-dimethylbenzonitrile → 4-(Aminomethyl)-2,6-dimethylaniline

HRID 1432066Notes

Reaction equation

HRID 1432066 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:15]([CH3:16])=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH3:17]>C1COCC1>[NH2:7][C:8]1[C:9]([CH3:17])=[CH:10][C:11]([CH2:12][NH2:13])=[CH:14][C:15]=1[CH3:16]

Participants

4

Reactant 2

HCID 2789444-amino-3,5-dimethylbenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 451166384-(Aminomethyl)-2,6-dimethylaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Step AN2. To the suspension of 0.26 g of lithium aluminum hydride in 30 mL of THF was added dropwise a solution of 0.49 g of 4-amino-3,5-dimethylbenzonitrile in 5 mL of THF. The reaction mixture was stirred at reflux for 3 hours and cooled to room temperature. The reaction mixture was quenched with 1.0 mL of 1.0 N NaOH aqueous solution. The precipitate was filtered off and the solvent was evaporated in vacuo to provide the crude product, which can be used without purification. A portion of the crude product was purified by preparative HPLC. LCMS (method B) RT 0.152 min., (2M+H)+ 301. 1H NMR (500 MHz, CD3OD) δ 7.04 (s, 2 H), 3.95 (s, 2 H), 2.25 (s, 6 H).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe reaction mixture was quenched with 1.0 mL of 1.0 N NaOH aqueous solution
  3. filtrationThe precipitate was filtered off
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-16fc17153949406d82e73255b4fd9c59
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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