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2-(1-Methylhydrazinyl)-3-(trifluoromethyl)pyridine → HCID 53949563, compound

HRID 1106708
Notes
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Reaction equation

HRID 1106708 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=O)[C:5](=[O:15])[N:4]([CH3:16])[N:3]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[C:20]([N:25]([CH3:27])[NH2:26])=[N:21][CH:22]=[CH:23][CH:24]=1>C(O)C.C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[N:26][N:25]([CH3:27])[C:20]2[C:19]([C:18]([F:29])([F:28])[F:17])=[CH:24][CH:23]=[CH:22][N:21]=2)[C:5](=[O:15])[N:4]([CH3:16])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 27777792-(1-Methylhydrazinyl)-3-(trifluoromethyl)pyridineHCID 18789809HCID 18789809, compound

Product 1

HCID 53949563HCID 53949563, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent2×
HCID 516892
Sodium Bicarbonate
Solvent

Conditions

Temperature
50 °C

Procedure

The title compound of Step A (0.20 g, 0.80 mmol) was dissolved in absolute ethanol (7 mL) and a solution of 1-[3-(trifluoromethyl)pyridin-2-yl]-1-methylhydrazine in ethanol (3 mL) was added followed by 3 drops of glacial acetic acid. The mixture was warmed to 50° C. for 1 h, cooled to room temperature and then diluted with aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined organic phases were dried (MgSO4), filtered and concentrated to give 0.38 g of the title compound of Step B as a yellow solid. 1H NMR (300 MHz. CDCl3): δ 8.42 (d.1H. J=5 Hz), 8.16 (d,1H, J=8 Hz), 8.01 (d,1H, J=8 Hz), 7.51 (t,1H, J=8 Hz), 7.42 (t,1H), J=8 Hz), 7.35 (s,1H), 7.21 (d,1H, J=8 Hz), 7.03 (dd,1H, J=8, 5 Hz), 3.56 (s,6H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a5a06c4bc3c411dbd7bff557fa6592a
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06057352

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes