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

HRID 1486741
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HRID 1486741 반응식
[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]
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6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eb6914f785924cd4995b7b0a29c67b71
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09428456B2

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