Hydrogen Bromide → 5-Amino-2-aminomethyl-pyridin-4-ol

HRID 2236546Notes

Reaction equation

HRID 2236546 reaction equation
C[O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][N:6]=[C:5]([CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH:4]=1.Br>>[NH2:9][C:8]1[C:3]([OH:2])=[CH:4][C:5]([CH2:12][NH2:13])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 687001092-(4-Methoxy-5-nitro-pyridin-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 1785102595-Amino-2-aminomethyl-pyridin-4-ol

Procedure

A mixture of 2-(4-methoxy-5-nitro-pyridin-2-ylmethyl)-isoindole-1,3-dione (0.24 g, 7.7 mmole) and 48% hydrobromic acid (3 mL), is refluxed for 3 hours. The reaction mixture is cooled, evaporated to dryness in vacuo, dissolved in absolute ethanol (25 mL) and 10% Palladium on carbon (100 mg) is added under an inert atmosphere. This is then hydrogenated on a Par apparatus at 45 psi for 2 hours. The reaction mixture is filtered and evaporated to give a brown solid, 60 mg, (23%), MS (ES+): m/z 140.2 (M+H). Used as is for the next step.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. customevaporated to dryness in vacuo
  4. dissolutiondissolved in absolute ethanol (25 mL)
  5. addition10% Palladium on carbon (100 mg) is added under an inert atmosphere
  6. filtrationThe reaction mixture is filtered
  7. customevaporated
  8. customto give a brown solid, 60 mg, (23%), MS (ES+)

Sources & evidence

ORD record
ord-869327628c2440739ab17c5d97fd63c3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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