Sodium Hydroxide → 2-(6-Bromopyridin-2-yl)propan-2-amine

HRID 1969452Notes

Reaction equation

HRID 1969452 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:11]C(=O)C)([CH3:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>Cl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:11])([CH3:9])[CH3:10])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86004847HCID 86004847, compound

Product 1

HCID 581294592-(6-Bromopyridin-2-yl)propan-2-amineYield 81.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Combine N-[1-(6-bromo-pyridin-2-yl)-1-methyl-ethyl]-acetamide (3.3 g, 12.8 mmol) with 5N HCl (200 mL) and reflux overnight. Cool, add ice and neutralize with 1:1 ice: 50% NaOH until the mixture turns cloudy. Extract with dichloromethane, dry (Na2SO4), and evaporate to give 1-(6-bromo-pyridin-2-yl)-1-methyl-ethylamine (2.24 g, 81%). MS (m/z) 215 and 217 (M+H)+.

Workup

  1. temperatureCool
  2. additionadd ice
  3. extractionExtract with dichloromethane
  4. dry with materialdry (Na2SO4)
  5. customevaporate

Sources & evidence

ORD record
ord-6560b6c1671b4b97af9f9aad0f845e13
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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