3-Cyanopyridine → HCID 178492293, compound

HRID 901927Notes

Reaction equation

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

Participants

Reactant 3

HCID 793-Cyanopyridine

HCID 7732P-Anisidine

HCID 253877Potassium Bromide

Product 1

HCID 178492293HCID 178492293, compoundYield 62.82%

Procedure

The title compound was prepared from 3-cyanopyridine (8.5 g, 83 mmol) and 4-methoxyaniline (10 g, 83 mmol) by following the procedure described in preparation 10 (11.6 g, yield 62.82%, mp 137-139° C., purity 97.2% by HPLC). 1H-NMR (CDCl3):δ 3.81 (s, 3H), 4.94 (bs, 2H, D2O exchangeable), 6.93 (s, 4H), 7.37-7.4 (d, 1H), 8.22-8.24 (d, 1H), 8.70-8.71 (d, 1H), 9.0 (s, 1H). IR (KBr) cm−1: 3281, 3085, 3001, 2960, 2937, 1660. MS m/z:228.2 (M+).

Workup

customdescribed in preparation 10 (11.6 g, yield 62.82%, mp 137-139° C., purity 97.2% by HPLC)

Sources & evidence

ORD record: ord-fe43b6f2213444b3a4f647098f3c0f41
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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