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Trichloroacetonitrile → 6-Chloro-2-methyl-3-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine

HRID 385958
Notes
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Reaction equation

HRID 385958 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[N:3]=1.[C:12]([NH:15][NH2:16])(=O)[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C#N>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:11])[C:5]([C:6]2[O:8][C:12]([CH3:13])=[N:15][N:16]=2)=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 14039AcetohydrazideHCID 462238396-Chloro-2-methylpyridine-3-carboxylic acid

Product 1

HCID 595258946-Chloro-2-methyl-3-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
150 °C

Procedure

6-Chloro-2-methylnicotinic acid (200 mg, 1.2 mmol), acetohydrazide (95 mg, 1.3 mmol), solid supported triphenylphosphine on polystyrene (1.88 mmol/g loading, 1.94 g, 3.5 mmol) were placed in a microwave vial. Dry acetonitrile (16.7 ml) followed by trichloroacetonitrile (0.23 ml, 2.33 mmol) were added and the vial was heated in a microwave at 150° C. for 20 minutes. It was allowed to cool to room temperature, filtered, and the filter cake was washed with acetonitrile. The filtrate was concentrated under reduced pressure to afford the title compound.

Workup

  1. additionwere added
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washthe filter cake was washed with acetonitrile
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2040867994ac483f83d997bbe8136a46
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367706B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes