2-Methylbenzonitrile → HCID 178438972, compound

HRID 925022

Reaction equation

HRID 925022 reaction equation
[CH2:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])[CH2:2][CH3:3].[CH2:11]([Li])CCC.[C:16]1(C)[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>>[CH2:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:22](=[NH:23])[C:17]1[CH:16]=[CH:21][C:20]([CH3:11])=[CH:19][CH:18]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 107212-MethylbenzonitrileHCID 157592-PropylanilineHCID 178418339Butyllithium

Product 1

HCID 178438972HCID 178438972, compound

Procedure

Procedure as described for Amidine X using the following amounts: 6.00 mL of 2-n-propylaniline (42.6 mmol); 21.3 mL of 2.0 M butyllithium (42.6 mmol); 5.00 g of toluonitrile (42.6 mmol). Filtration of the final pentane solution yielded 9.53 g (89%) of light yellow solid. 1H NMR (400 MHz, CDCl3): 7.76 (d, 2H), 7.22 (m, 3H), 7.15 (t, 1H), 6.99 (t, 1 H), 6.84 (d, 1 H), 4.69 (s, 2H), 2.51 (t, 2H), 2.39 (s, 3H), 1.58 (m, 2H), 0.90 (t, 3H).

Workup

  1. filtrationFiltration of the final pentane solution
  2. customyielded 9.53 g (89%) of light yellow solid

Sources & evidence

ORD record
ord-e0d891a106aa406eb2ccfab43963ceaf
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Linked notes

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