Hydrazine hydrate (1:1) → HCID 59548015, compound

HRID 1946319Notes

Reaction equation

HRID 1946319 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][N:16]2[CH:20]=[CH:19][C:18]([N:21]3C(=O)C4C(=CC=CC=4)C3=O)=[N:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C1COCC1>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][N:16]2[CH:20]=[CH:19][C:18]([NH2:21])=[N:17]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66790255HCID 66790255, compound

Product 1

HCID 59548015HCID 59548015, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[1-({2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-1H-isoindole-1,3(2H)-dione (4.83 g, approx 11.8 mmol) in THF (50 ml) was added hydrazine hydrate (2.86 ml, 59 mmol) and the solution was stirred overnight at ambient temperature. A white solid was filtered off and the filtrate dried over magnesium sulphate, filtered and evaporated to give an oil. The oil was applied to 100 g silica and purified using 0-100% ethyl acetate-cyclohexane to give the title compound as a pale yellow oil (1.66 g); LCMS: (System 3) MH+=280, tRET=0.96 min.

Workup

  1. filtrationA white solid was filtered off
  2. dry with materialthe filtrate dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. custompurified

Sources & evidence

ORD record
ord-803a56e51a4f49008d6cb7267f379ae6
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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