Hydrazine → HCID 55285625, compound

HRID 2280711Notes

Reaction equation

HRID 2280711 reaction equation
[OH:1][C@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:3]1.O.NN.NN>CO>[NH2:9][C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:2]([OH:1])[CH2:3]1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 71237312HCID 71237312, compound

Product 1

HCID 55285625HCID 55285625, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-((1R,3S)-3-Hydroxycycloheptyl)-isoindoline-1,3-dione (1800 mg, 6.94 mmol) was dissolved in methanol (86.80 mL). Hydrazine monohydrate (0.354 mL, 7.29 mmol) was added to the solution and the resulting mixture was stirred overnight at reflux. An additional 0.2 eq (0.067 mL) of hydrazine was added and the mixture was refluxed for a second night. The reaction mixture was concentrated to a volume of a few milliliters and filtered. The solids were rinsed with 50 mL each of DCM and chloroform and the resulting filtrate concentrated under reduced pressure to afford the title compound (174 mg, 1.347 mmol, 19.40% yield) as an oil that was used without further purification. MS (ESI) m/z 130.2 [M+H]+.

Workup

  1. temperatureat reflux
  2. temperaturethe mixture was refluxed for a second night
  3. concentrationThe reaction mixture was concentrated to a volume of a few milliliters
  4. filtrationfiltered
  5. washThe solids were rinsed with 50 mL each of DCM and chloroform
  6. concentrationthe resulting filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-2aa0e25d50f74d74a53f6ac45885c860
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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