Ammonia → HCID 54355418, compound

HRID 2286712Notes

Reaction equation

HRID 2286712 reaction equation
[NH2-:1].[Na+].[NH3:3].[CH3:4][N:5]([CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:13][CH2:14][CH2:15][CH2:16][CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:18][CH2:19][CH2:20][CH3:21].[H][H]>[Fe].O>[CH3:13][CH2:14][CH2:15][CH2:16][CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:18][CH2:19][CH2:20][CH3:21].[NH2:1][C:4]1[C:22]([CH:17]([CH2:16][CH2:15][CH2:14][CH3:13])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:27][CH:26]=[CH:25][N:3]=1.[CH3:13][CH2:14][CH2:15][CH2:16][CH:17]([C:22]1[N:23]=[C:24]([C:7]2[CH:15]=[CH:14][CH:13]=[C:9]([CH:10]([CH2:11][CH2:6][CH2:5][CH3:12])[CH2:16][CH2:17][CH2:18][CH3:19])[N:8]=2)[CH:25]=[CH:26][CH:27]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

10

Reactant 5

HCID 222Ammonia2×HCID 949N,N-DimethylanilineHCID 24533Sodium amideHCID 137778Pyridine, 2-(1-butylpentyl)-HCID 178418361HCID 178418361, compound2×

Product 3

HCID 137778Pyridine, 2-(1-butylpentyl)-HCID 234620936,6′-Bis(1-butylpentyl)-2,2′-bipyridineHCID 54355418HCID 54355418, compoundYield 2.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
152 °C

Procedure

In a two-liter, three-neck flask, equipped with a stirrer and dropping funnel, was prepared 0.20 mole of sodamide, using an iron catalyst, in about 600 cc of liquid ammonia. The ammonia was replaced by adding 1,000 g of N,N-dimethylaniline through the dropping funnel and evaporating the ammonia. A thermometer and reflux condenser were added to the flask. The mixture was heated to 152° C. and 205 g (1.0 mole) of 2-(5-nonyl)pyridine was added. No reaction took place. The mixture was slowly heated to 197° C. when hydrogen evolution started, and the reaction mixture turned purple. The reaction continued at 197°-198° C. for 3 hours, at which time the hydrogen evolution became slow. The reaction mixture was cooled to about room temperature and hydrolyzed with 200 cc of water. The oil layer was separated and distilled to give 125 g (0.61 mole) of unreacted 2-(5-nonyl)pyridine, B 2.3 g (0.01 mole) of 2-amino-(5-nonyl)pyridine (2.7% yield) and 35.8 g (0.09 mole) of 6,6'-di-(5-nonyl)-2,2'-bipyridyl boiling at 251°-259° C. and 7 mm Hg. The yield of 2,2'-bipyridyl product based on recovered 2-(5-nonyl)pyridine was 45.0%.

Workup

  1. customIn a two-liter, three-neck flask, equipped with a stirrer
  2. customevaporating the ammonia
  3. temperatureA thermometer and reflux condenser
  4. additionwere added to the flask
  5. customThe oil layer was separated
  6. distillationdistilled

Sources & evidence

ORD record
ord-9d226b7475ab4156a806f5a0cfaba462
Source dataset
uspto-grants-1981_05
Patent number
US04267335

Reaction notes

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