Pyridine-2-carbonitrile → HCID 178492292, compound

HRID 901918Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=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:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[NH:2])=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 7522Pyridine-2-carbonitrile

HCID 7732P-Anisidine

HCID 253877Potassium Bromide

Product 1

HCID 178492292HCID 178492292, compoundYield 86.7%

Procedure

The title compound was prepared from 2-cyanopyridine (8.46 g, 81 mmol) and 4-methoxyaniline (10 g, 81 mmol) by following the procedure described in preparation 10 (16 g, yield 86.7%, mp 73-75° C., purity 97.6% by HPLC). 1H-NMR (CDCl3):δ 3.81 (s, 3H), 5.5-6 (bs, 2H, D2O exchangeable), 6.91-6.98 (m, 4H), 7.37-7.4 (m, 1H), 7.79-7.83 (m, 1H), 8.39-8.41 (d, 1H), 8.56-8.57 (d, 1H). IR (KBr) cm−1: 3456, 3540, 3410, 1663. MS m/z:228.2 (M+).

Workup

customdescribed in preparation 10 (16 g, yield 86.7%, mp 73-75° C., purity 97.6% by HPLC)

Sources & evidence

ORD record: ord-a7c8acb839b6476a91fcfb56e265bab8
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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