3,4-Dimethylaniline → HCID 178426509, compound

HRID 901919Notes

Reaction equation

HRID 901919 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[CH3:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[CH3:17])[NH2:13].[K+].[Br-]>>[CH3:9][C:10]1[CH:11]=[C:12]([NH:13][C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[NH:2])[CH:14]=[CH:15][C:16]=1[CH3:17]

Participants

4

Reactant 3

HCID 72483,4-DimethylanilineHCID 7522Pyridine-2-carbonitrileHCID 253877Potassium Bromide

Product 1

HCID 178426509HCID 178426509, compoundYield 71.2%

Procedure

The title compound was prepared from 2-cyanopyridine (8.6 g, 83 mmol) and 3,4-dimethylaniline (10 g, 83 mmol) by following the procedure described in preparation 10 (13.2 g, yield 71.2%, mp 105-107° C., purity 99.9% by HPLC). 1H-NMR (CDCl3): δ 2.24-2.25 (d, 6H), 5.75-6 (bs, 2H, D2O exchangeable), 6.75-6.81 (m, 2H), 7.11-7.13 (d, 1H), 7.36-7.39 (m, 1H), 7.78-7.82 (m, 1H) 8.39-8.41 (d, 1H), 8.55-8.57 (m, 1H). IR (KBr) cm−1: 3445, 3303, 1645, 1625. MS m/z:227 (M+).

Workup

  1. customdescribed in preparation 10 (13.2 g, yield 71.2%, mp 105-107° C., purity 99.9% by HPLC)

Sources & evidence

ORD record
ord-3296cceaa5644d5e8c30532a89211013
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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