Hydrazine hydrate (1:1) → Ethyl 4-amino-1-methylcyclohexanecarboxylate

HRID 712246Notes

Reaction equation

HRID 712246 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:17][CH2:16][C:15]([CH3:23])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.O.NN>CCO>[NH2:3][CH:12]1[CH2:13][CH2:14][C:15]([CH3:23])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58074352Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate

Product 1

HCID 58291914Ethyl 4-amino-1-methylcyclohexanecarboxylateYield 102.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To an ice-cold solution of ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate (0.30 g, 0.95 mmol) in EtOH (20 mL) was added hydrazine hydrate (0.115 mL, 2.38 mmol) and the resulting mixture heated up to 80° C. for 2-3 h. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL), extracted with EtOAc (3×50 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product as a viscous liquid (0.18 g, crude). MS: 186.20 [M+H]+.

Workup

  1. customAfter the completion of reaction (by TLC), solvent
  2. customwas evaporated under reduced pressure, water
  3. additionadded (20 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. washthe combined organics washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58995befabf04873baa998ee9c2472fe
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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