3-Cyanopyridine → HCID 178436604, compound

HRID 901925Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[CH2:9]([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)[CH3:10].[K+].[Br-]>>[CH2:9]([C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[NH:2])=[CH:13][CH:12]=1)[CH3:10]

Participants

Reactant 3

HCID 793-Cyanopyridine

HCID 115044-Ethylaniline

HCID 253877Potassium Bromide

Product 1

HCID 178436604HCID 178436604, compoundYield 84.9%

Procedure

The title compound was prepared from 3-cyanopyridine (8.5 g, 83 mmol) and 4-ethylaniline (10 g, 83 mmol) by following the procedure described in preparation 10 (15.8 g, yield 84.9%, mp 134-136 C, purity 99.8% by HPLC). 1H-NMR (CDCl3):δ 1.22-1.26 (t, 3H), 2.60-2.65 (q, 2H), 5.09 (bs, 2H, D2O exchangeable), 6.88-6.89 (d, 2H), 7.18-7.19 (d, 2H), 7.32-7.35 (m, 1H), 8.18-8.20 (d, 1H), 8.64-8.65 (d, 1H), 9.03 (s, 1H). IR (KBr) cm−1: 3302, 3108, 2965, 2928, 2844, 1655. MS m/z: 227.1 (M+).

Workup

customdescribed in preparation 10 (15.8 g, yield 84.9%, mp 134-136 C, purity 99.8% by HPLC)

Sources & evidence

ORD record: ord-d2fefd48efb841d8adbd6898a9c46cf8
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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