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

HRID 1797083Notes

Reaction equation

HRID 1797083 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 example1, 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-17958fd5fb3f4a29b146a0d76aff3c59
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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