Hydrochloric Acid → 6-(2-p-Tolyl-vinyl)-pyridin-2-yl-amine hydrochloride

HRID 965854Notes

Reaction equation

HRID 965854 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[N:14]=[C:13](C(O)=O)[CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C([N:21](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[ClH:43]>CCOC(C)=O.CCCCCC.CCN(CC)CC.C(O)CCC>[ClH:43].[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[N:14]=[C:13]([NH2:21])[CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 695920816-(2-p-Tolyl-vinyl)-pyridine-2-carboxylic acid

Product 1

HCID 695920206-(2-p-Tolyl-vinyl)-pyridin-2-yl-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 22141343EtOAc hexane triethylamineSolvent

Procedure

In a variation to the procedure referred to in example 1, 6-(2-p-tolyl-vinyl)-pyridine-2-carboxylic acid (2.81 g, 11.7 mmol) was brought to reaction with triethylamine (1.21 g, 12.0 mmol), diphenyl phosphoryl azide (3.56 g, 12.9 mmol) and butanol (33 ml). After extractive workup the residue was refluxed (4 hr) with 3N HCl. Extractive workup and chromatography (SiO2 with AcOEt/hexane/NEt3=10:20:1) afforded the title compound as an oil which was crystallized as the yellow hydrochloride salt (0.95 g, 33%). Mp.>250° C. (MeOH/Et2O), MS: m/e=210 (M+).

Sources & evidence

ORD record
ord-8fe665156cff45cebd8d698ef5d6626c
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Reaction notes

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