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

HRID 1486741
Notes
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Reaction equation

HRID 1486741 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86706559N-(3-[1,3]Dioxolan-2-yl-phenyl)-5-methyl-nicotinamide

Product 1

HCID 86706560N-(3-Formyl-phenyl)-5-methyl-nicotinamide

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

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

  1. customto get pH 10
  2. extractionThe mixture is extracted twice with EtOAc (100 mL)
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes