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Hydrazine hydrate (1:1) → 2-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridine-4-carboxylic acid hydrazide

HRID 500539
Notes
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Reaction equation

HRID 500539 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:8](=[O:20])[CH:7]=1)=O)C.O.[NH2:22][NH2:23]>C(O)C>[O:20]=[C:8]1[CH:7]=[C:6]([C:4]([NH:22][NH2:23])=[O:3])[CH:11]=[CH:10][N:9]1[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 248517012-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridine-4-carboxylic acid ethyl ester

Product 1

HCID 684588242-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridine-4-carboxylic acid hydrazideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

The title compound of example 19.1 (9.5 g, 32 mmol) was stirred in ethanol (100 mL) at 78° C. Hydrazine hydrate (7.8 mL, 159.7 mmol) was added and the reaction mixture was stirred at 78° C. for 3 hours. The reaction mixture was cooled to room temperature and concentrated to dryness. The residue was stirred in diethyl ether and filtered to give a yellow solid (8.5 g, 94%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. stirringThe residue was stirred in diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0c89a5ba875e446d8386c2573be52106
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772235B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes