3-Cyanopyridine → HCID 178426510, compound

HRID 901926Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=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:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[NH:2])[CH:14]=[CH:15][C:16]=1[CH3:17]

Participants

Reactant 3

HCID 793-Cyanopyridine

HCID 72483,4-Dimethylaniline

HCID 253877Potassium Bromide

Product 1

HCID 178426510HCID 178426510, compoundYield 84%

Procedure

The title compound was prepared from 3-cyanopyridine (8.6 g, 83 mmol) and 3,4-dimetylaniline (10 g, 83 mmol) by following the procedure described in preparation 10 (15.6 g, yield 84%, mp 132-134 C, purity 99.7% by HPLC). 1H-NMR (CDCl3):δ 2.24-2.26 (d, 6H), 4.92 (bs, 2H, D2O exchangeable), 6.72-6.74 (d, 1H), 6.78 (s, 1H), 7.11-7.13 (d, 1H), 7.36-74 (m, 1H), 8.22-8.24 (d, 1H), 8.69-8.7 (d, 1H), 9.06 (d, 1H). IR (KBr) cm−1: 3313, 3142, 2997, 2958, 2918, 1651. MS m/z:226.1 (M+).

Workup

customdescribed in preparation 10 (15.6 g, yield 84%, mp 132-134 C, purity 99.7% by HPLC)

Sources & evidence

ORD record: ord-699c59a411d544ce95d07a99f8d633dd
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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