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Hydrochloric Acid → (E)-3-[6-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-pyridin-3-yl]acrylic acid

HRID 2265084
Notes
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Reaction equation

HRID 2265084 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)=[O:7].[OH-].[Na+].Cl>C(O)C>[CH3:30][Si:2]([CH3:1])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86644273(E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylate

Product 1

HCID 59446288(E)-3-[6-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-pyridin-3-yl]acrylic acidYield 41%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

Compound 1b (232 mg) was dissolved in ethanol (7.89 ml). A 2N sodium hydroxide aqueous solution (5.26 ml) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution (5.26 ml) was added to neutralize the mixture. Then the solvent was distilled off. The reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution (0.5 ml) was added to adjust the pH of the mixture to 1. The mixture was stirred for 1 hour. The precipitated solid was filtered off and vacuum-dried to give Compound 1 (88.0 mg, 41%) as a white solid.

Workup

  1. temperaturecooled
  2. distillationThen the solvent was distilled off
  3. temperaturecooled
  4. additiona 2N hydrochloric acid aqueous solution (0.5 ml) was added
  5. stirringThe mixture was stirred for 1 hour
  6. filtrationThe precipitated solid was filtered off
  7. customvacuum-dried

Sources & evidence

ORD record
ord-be65e00901654df79e4a3324fcca969c
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07855300B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes