tert-Butylhydrazine → HCID 66804019, compound

HRID 594942Notes

Reaction equation

HRID 594942 reaction equation
[C:1]([CH:9]1[C:14](=O)[CH2:13][CH2:12][CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:20]([NH:24][NH2:25])([CH3:23])([CH3:22])[CH3:21]>C(O)C>[C:20]([N:24]1[C:14]2[CH2:13][CH2:12][CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10][C:9]=2[C:1]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[N:25]1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 81890tert-ButylhydrazineHCID 66801154HCID 66801154, compound

Product 1

HCID 66804019HCID 66804019, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 3-isonicotinoyl-4-oxocyclohexanecarboxylate (6.3 g, 24.3 mmol) and TEA (10.15 ml) in ethanol was added t-Butyl hydrazine (6.4 g, 73 mmol). The reaction mixture was stirred at room temperature for overnight. The solvent was removed under vacuum and DCM (50 ml) was added, followed by water (50 ml). The organic layer was collected, washed with brine and dried over sodium sulfate. Removal of solvent gave the desired product (6.5 g). LC-MS found 314.2 (M+H)

Workup

  1. customThe solvent was removed under vacuum and DCM (50 ml)
  2. additionwas added
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-4f5c3bd82d8048ec840c3bd0ff42b195
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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