Hydrochloric Acid → N-(3-Formyl-phenyl)-5-methyl-nicotinamide

HRID 1486741Notes

Reaction equation

[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[N:16][CH:15]=2)[CH:9]=[CH:10][CH:11]=1.Cl.O.[OH-].[Na+]>O1CCOCC1>[CH:2]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[N:16][CH:15]=2)[CH:9]=[CH:10][CH:11]=1)=[O:1]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-(3-[1,3]dioxolan-2-yl-phenyl)-5-methyl-nicotinamide (3.0 g, 10.55 mmol) in dioxane (50 mL) is treated with a 4M HCl in 1,4-dioxane (30 mL). The mixture is heated at 60° C. for 3 h. Water (100 mL) is added to the mixture followed by NaOH 2M (70 mL) solution to get pH 10. The mixture is extracted twice with EtOAc (100 mL). The combined organic phases are dried over MgSO4, filtered and evaporated. The crude title compound is obtained as a brownish solid (1.744 g. 69%) LC-MS A: tR=0.58 min; [M+H]+=241.24.

Workup

customto get pH 10
extractionThe mixture is extracted twice with EtOAc (100 mL)
dry with materialThe combined organic phases are dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-eb6914f785924cd4995b7b0a29c67b71
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428456B2

Reaction notes

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