Sodium Carbonate → 6-Chloro-N-(2,2-dimethylpropyl)-3-nitro-2-pyridinamine

HRID 729987Notes

Reaction equation

HRID 729987 reaction equation
[CH2:1]([NH2:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10]([Cl:17])[N:9]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[Cl:17][C:10]1[N:9]=[C:8]([NH:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 79882NeopentylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 611678716-Chloro-N-(2,2-dimethylpropyl)-3-nitro-2-pyridinamineYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Add neopentylamine (18 mL, 150 mmol) to a suspension of 2,6-dichloro-3-nitropyridine (20 g, 103 mmol) and Na2CO3 (18.5 g, 175 mmol) in EtOH (1.6 mL/mmol) at RT and stir overnight. Concentrate and dilute the resultant slurry with water (100 mL) and slowly neutralize with concentrated HCl (approx. 40 mL) to pH=7. Cool the suspension at 0° C. for 1 h and collect solid by vacuum filtration. Wash the solid with ice water (4×50 mL) and air dry overnight. Recrystallize the material from EtOAc and hexanes to give the title compound as a yellow solid (21.23 g, 84%).

Workup

  1. concentrationConcentrate
  2. additiondilute the resultant slurry with water (100 mL)
  3. customcollect solid
  4. filtrationby vacuum filtration
  5. washWash the solid with ice water (4×50 mL) and air
  6. customdry overnight
  7. customRecrystallize the material from EtOAc and hexanes

Sources & evidence

ORD record
ord-fa6d1934ea5d49e08aed87411f7a034f
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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