Hydrazine hydrate (1:1) → HCID 57458151, compound

HRID 1693062Notes

Reaction equation

HRID 1693062 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([CH3:22])=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>CO>[Cl:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([CH3:22])=[CH:16][C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57458152HCID 57458152, compound

Product 1

HCID 57458151HCID 57458151, compoundYield 127.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Chloro-4-methoxy-5-methylbenzyl)isoindoline-1,3-dione (174 mg, 0.55 mmol) was dissolved in MeOH (30 ml) and hydrazine hydrate (111 mg, 2.21 mmol) and then heated under reflux for 1 hour. The solvent was removed in vacuo and the precipitate was filtered off. The filtrate was evaporated to give a residue, which was chromatographed on a column of silica gel eluting with MeOH-DCM (1:10) to give the title compound (130 mg, 100%) as white solid. 1H NMR (270 MHz, DMSO-d6) δ ppm 2.12 (3H, s), 3.38 (2H, br s), 3.69 (2H, s), 3.78 (3H, s), 6.94 (1H, s), 7.29 (1H, s). MS (ESI) m/z 169 (M+H—NH2)+

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solvent was removed in vacuo
  3. filtrationthe precipitate was filtered off
  4. customThe filtrate was evaporated
  5. customto give a residue, which
  6. customwas chromatographed on a column of silica gel eluting with MeOH-DCM (1:10)

Sources & evidence

ORD record
ord-725d8c304fea41e5a0b05303134a88a2
Source dataset
uspto-grants-2012_04
Patent number
US08158650B2

Reaction notes

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