Hydrazine hydrate (1:1) → 2,6-Dichloro-4-methoxy-benzylamine hydrochloride

HRID 1670814Notes

Reaction equation

HRID 1670814 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([Cl:22])[C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([Cl:22])[C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 673536412-(2,6-Dichloro-4-methoxy-benzyl)-isoindole-1,3-dione

Product 1

HCID 673555502,6-Dichloro-4-methoxy-benzylamine hydrochlorideYield 166.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a solution of 2-(2,6-Dichloro-4-methoxy-benzyl)-isoindole-1,3-dione (2.74 g, 8.18 mmol) in ethanol with hydrazine hydrate (0.61 g, 12.27 mmol) at 70° C. for 12 hours. Cool the reaction and filter the precipitate. Concentrate the filtrate and partition the residue with ethyl acetate and water. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. To the residue, add ethyl acetate (20 mL) and HCl (4 N in dioxane, 5 mL). Collect the white crystal by filtration and air dry to afford 1.65 g (84%) of the title compound. MS (m/z): 242 (M+H)+.

Workup

  1. temperatureCool
  2. customthe reaction
  3. filtrationfilter the precipitate
  4. concentrationConcentrate the filtrate
  5. custompartition the residue with ethyl acetate and water
  6. dry with materialAfter drying the organic layer over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum
  9. additionTo the residue, add ethyl acetate (20 mL) and HCl (4 N in dioxane, 5 mL)
  10. customCollect the white crystal
  11. filtrationby filtration and air
  12. customdry

Sources & evidence

ORD record
ord-ba017527473d4b31accd5399dc407ed1
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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