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Acetic Acid → 1,2,5,6-Tetrahydro-N-hydroxy-1-methyl-2-oxo-3-pyridinepropanamide

HRID 2240611
Notes
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Reaction equation

HRID 2240611 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:13])[N:8]([CH3:12])[CH2:9][CH2:10][CH:11]=1.[NH2:15][O:16][K].C(O)(=O)C>CO.C(OCC)(=O)C>[OH:16][NH:15][C:3](=[O:2])[CH2:4][CH2:5][C:6]1[C:7](=[O:13])[N:8]([CH3:12])[CH2:9][CH2:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 16720334HCID 16720334, compoundHCID 178514655HCID 178514655, compound

Product 1

HCID 114129481,2,5,6-Tetrahydro-N-hydroxy-1-methyl-2-oxo-3-pyridinepropanamideYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

50 mg of 3-(1-methyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester prepared from the above Step 1 was dissolved in methanol (0.25 mM) and then 0.122 ml of 1.7M NH2OK suspension solution in methanol (0.207 mM) was added thereto at 0° C. and the resulting mixture was stirred for 3 hrs at room temperature. The resulting mixture was neutralized with 0.02 ml of acetic acid, diluted with 10 ml of ethyl acetate, filtered and concentrated in vacuo. The resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:20) solvent mixture as an eluant to give 19 mg of the title compound (j2) (yield: 35%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:20) solvent mixture as an eluant

Sources & evidence

ORD record
ord-5077e34e76a2477fa6fdb510c5f28b8e
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723376B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes