Sodium Bicarbonate → 6-(2-Aminopropan-2-yl)picolinonitrile

HRID 1969458Notes

Reaction equation

HRID 1969458 reaction equation
Cl.[NH2:2][C:3]([C:6]1[N:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4].C(=O)(O)[O-].[Na+]>ClCCl>[NH2:2][C:3]([C:6]1[N:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][CH:7]=1)([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 665706716-(2-Aminopropan-2-yl)pyridine-2-carbonitrile--hydrogen chloride (1/1)

Product 1

HCID 581295196-(2-Aminopropan-2-yl)picolinonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Partitioned 6-(1-amino-1-methyl-ethyl)-pyridine-2-carbonitrile hydrochloride salt (880 mg, 3.8 mmol) between dichloromethane and 10% aqueous sodium bicarbonate (10 mL). Separate the layers and extract with dichloromethane (3×10 mL). Dry the organic extracts (Na2SO4) and evaporate to give 6-(1-amino-1-methyl-ethyl)-pyridine-2-carbonitrile in quantitative yield. 1H NMR (400 MHz, CDCl3) δ 7.76-7.68 (m, 2H), 7.50 (d, J=7.5 Hz, 1H), 1.87-1.80 (m, 2H), 1.47 (s, 6H).

Workup

  1. customSeparate the layers
  2. extractionextract with dichloromethane (3×10 mL)
  3. dry with materialDry the organic extracts (Na2SO4)
  4. customevaporate

Sources & evidence

ORD record
ord-2eca41ddd16b48cab2823d8b4fb515db
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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