4-Cyanopyridine → HCID 178426512, compound

HRID 901923Notes

Reaction equation

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

Participants

Reactant 3

HCID 75064-Cyanopyridine

HCID 7813p-Toluidine

HCID 253877Potassium Bromide

Product 1

HCID 178426512HCID 178426512, compoundYield 72.5%

Procedure

The title compound was prepared from 4-cyanopyridine (9.72 g, 93 mmol) and 4-methylaniline (10 g, 93 mmol) by following the procedure described in preparation 10 (14.3 g, yield 72.5%, mp 120-123° C., purity 98.75% by HPLC). 1H-NMR (CDCl3):δ 2.33 (s, 3H), 5.06 (bs, 2H, D2O exchangeable), 6.84-6.86 (d, 2H), 7.16-7.18 (d, 2H), 7.71-7.72 (d, 2H), 8.66-8.67 (d, 2H). IR (KBr) cm−1: 3437, 3138, 1644. MS m/z:212.1 (M+).

Workup

customdescribed in preparation 10 (14.3 g, yield 72.5%, mp 120-123° C., purity 98.75% by HPLC)

Sources & evidence

ORD record: ord-816b45313137411c94a9b922be78d8d1
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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