Hydrazine hydrate (1:1) → 6-Bromo-2-Pyridinemethanamine

HRID 29260Notes

Reaction equation

HRID 29260 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH2:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 221764462-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 187718616-Bromo-2-PyridinemethanamineYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2-(6-Bromo-pyridin-2-ylmethyl)-isoindole-1,3-dione (4000 mg, 12.61 mmol) in ethanol (60 mL ) was heated at 70° C. until complete dissolution was observed. Hydrazine hydrate (3156 mg, 63.06 mmol) was then added and the resulting mixture was heated at 70° C. for 5 h. The resulting solution was cooled to 0° C. and filtered. The filtrate was concentrated in vacuo and the crude residue was purified by column chromatography with a gradient of 0 to 30% methanol/dichloromethane to give C-(6-Bromo-pyridin-2-yl)-methylamine as a yellow solid (2070 mg, 79%). MS ES (MH+187.1, RT=1.11 min).

Workup

  1. temperaturethe resulting mixture was heated at 70° C. for 5 h
  2. temperatureThe resulting solution was cooled to 0° C.
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude residue was purified by column chromatography with a gradient of 0 to 30% methanol/dichloromethane

Sources & evidence

ORD record
ord-9e9d8b3551b0470baf8cb30ff40d5dcd
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Reaction notes

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