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

HRID 2261407
Notes
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Reaction equation

HRID 2261407 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.CO.[NH2:17][O:18][K].C(O)(=O)C>C(OCC)(=O)C>[OH:18][NH:17][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 4

HCID 176Acetic AcidHCID 887Methanol2×HCID 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 1

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 mmol) and then 0.12 ml of 1.7M NH2OK suspension solution in methanol (0.21 mmol) 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 (yield: 35%) of the title compound (j2).

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-4c2cc5b17a38433099080b57bf09b5f5
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846963B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes