Hydrazine hydrate (1:1) → (3-Bromo-5-chlorophenyl)methanamine

HRID 917542Notes

Reaction equation

HRID 917542 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][N:6]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 589629502-(3-Bromo-5-chlorobenzyl)isoindoline-1,3-dione

Product 1

HCID 58962965(3-Bromo-5-chlorophenyl)methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Step G4. A mixture of 2-(3-Bromo-5-chlorobenzyl)isoindoline-1,3-dione (5.1 g, 14.6 mmol) and hydrazine monohydrate (0.8 g, 16 mmol) in ethanol (150 mL) was refluxed for 4 hours. Upon cooling to room temperature, a white solid precipitated. The solid was filtered and washed with ethanol, then dried in vacuum. 1H NMR (DMSO-d6) showed that the white solid is a mixture of 3-bromo-5-chlorobenzylamine and 2,3-dihydrophthalazine-1,4-dione. This material was used in subsequent steps without further purification.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customa white solid precipitated
  3. filtrationThe solid was filtered
  4. washwashed with ethanol
  5. customdried in vacuum
  6. additiona mixture of 3-bromo-5-chlorobenzylamine and 2,3-dihydrophthalazine-1,4-dione
  7. customThis material was used in subsequent steps without further purification

Sources & evidence

ORD record
ord-086b5dee3148436695449a0298264bf7
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

Loading…