Hydrochloric Acid → HCID 68981936, compound

HRID 1821811Notes

Reaction equation

HRID 1821811 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:20]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7656DibenzylamineHCID 10340Sodium CarbonateHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 68981936HCID 68981936, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-chloro-4-methyl-5-nitropyridine (5.44 g, 26.3 mmol) and dibenzylamine (5.04 mL, 26.3 mmol) in toluene (13.1 mL) was added sodium carbonate (5.58 g, 52.6 mmol). After stirring under a nitrogen atmosphere under reflux for 36 h, the reaction mixture was filtered to remove the sodium carbonate. The filtrate was concentrated to provide the crude material as a light orange oil. The crude oil was dissolved in methylene chloride and treated with 2 N HCl. The resulting precipitate was filtered off and discarded. The filtrate was washed with 2 N HCl and the acidic layers were back-extracted with methylene chloride. The combined extracts were washed with saturated NaHCO3, dried over Na2SO4, filtered and concentrated to provide 2-(dibenzylamino)-5-nitro-4-methylpyridine (8.97 g, 102% theoretical) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ2.53 (3H, s), 4.85 (4H, s), 6.27 (1H, s), 7.19-7.37 (10H, m), 9.05 (1H, s).

Workup

  1. temperatureunder reflux for 36 h
  2. filtrationthe reaction mixture was filtered
  3. customto remove the sodium carbonate
  4. concentrationThe filtrate was concentrated
  5. customto provide the crude material as a light orange oil
  6. filtrationThe resulting precipitate was filtered off
  7. washThe filtrate was washed with 2 N HCl
  8. extractionthe acidic layers were back-extracted with methylene chloride
  9. washThe combined extracts were washed with saturated NaHCO3
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-1d7a88f3f00845e8a72561d3aed99d07
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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