Hydrazine hydrate (1:1) → HCID 178494298, compound

HRID 510437Notes

Reaction equation

HRID 510437 reaction equation
[Cl:1][C:2]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[C:6]([O:21][CH3:22])=[N:7][NH:8][C:9]=1[N:10]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C1COCC1>[Cl:1][C:2]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[C:9]([NH2:10])=[N:8][NH:7][C:6]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 71270835HCID 71270835, compound

Product 1

HCID 178494298HCID 178494298, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(2,3-dichlorobenzyl)-3-methoxy-1H-pyrazol-5-yl)isoindoline-1,3-dione (620 mg, 1.54 mmol) in THF (20 mL) was added hydrazine hydrate (1.0 g, 20 mmol) dropwise with stirring at room temperature. Then, the mixture was stirred at room temperature for 2 hours and 50° C. for another 2 hours. Then the reaction mixture was concentrated under vacuo and the residue was purified by silica gel chromatography eluted with EA to give the titled compound (301 mg, 72%) as a colorless viscous liquid. LC/MS: MS (ES+) m/e 272 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 3.71 (s, 2H), 3.86 (s, 3H), 7.07-7.14 (m, 2H), 7.29-7.32 (m, 1H).

Workup

  1. stirringThen, the mixture was stirred at room temperature for 2 hours and 50° C. for another 2 hours
  2. concentrationThen the reaction mixture was concentrated under vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluted with EA

Sources & evidence

ORD record
ord-dde1abebe0de46ec90a030d1dc9e2ac0
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

Loading…