Ammonia → HCID 23462097, compound

HRID 1447709Notes

Reaction equation

HRID 1447709 reaction equation
[NH2-:1].[Na+].N.[CH2:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[H][H]>O.C1(C)C(C)=CC=CC=1>[CH2:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[NH2:1][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[N:10]=1.[CH2:4]([C:9]1[N:10]=[C:11]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[N:1]=2)[CH:12]=[CH:13][CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 222Ammonia2×HCID 24533Sodium amideHCID 814542-IsopentylpyridineHCID 178418361HCID 178418361, compound

Product 3

HCID 814542-IsopentylpyridineHCID 23462097HCID 23462097, compoundYield 38.9%HCID 234620996-(3-Methylbutyl)-2-pyridinamineYield 8.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

In a 300 cc, three-neck flask, equipped with a stirrer and dropping funnel, was made 0.2 mole of sodamide in liquid ammonia. The ammonia was replaced with 100 cc of xylene. A thermometer and reflux condenser were attached to the reaction flask, and the mixture was heated to reflux. Under reflux, 24.1 g (0.16 mole) of 2-isoamylpyridine was added from the dropping funnel. The reaction mixture turned to a deep purple and hydrogen began evolving. Refluxing was continued for 6.5 hours. The temperature range was 140°-146° C. At the end of the reflux, the reaction mixture was cooled to about 100° C. and hydrolyzed with 50 cc of water. The oil layer was separated at room temperature and the aqueous layer was extracted with 22 cc of xylene. The oil layer and xylene extract were distilled through a Vigreaux column to give 15.3 g of 2-isoamylpyridine (0.10 mole), 0.8 g of 2-amino-6-isoamylpyridine (8.2% yield) and 3.4 g of 6,6'-di-isoamyl-2,2'-bipyridyl (38.9% yield).

Workup

  1. customIn a 300 cc, three-neck flask, equipped with a stirrer
  2. temperatureA thermometer and reflux condenser
  3. temperaturethe mixture was heated to reflux
  4. temperatureUnder reflux
  5. temperatureRefluxing
  6. customwas 140°-146° C
  7. customThe oil layer was separated at room temperature
  8. extractionthe aqueous layer was extracted with 22 cc of xylene
  9. extractionThe oil layer and xylene extract
  10. distillationwere distilled through a Vigreaux column

Sources & evidence

ORD record
ord-d406c02a1ec04c0cb5559a81f10edd04
Source dataset
uspto-grants-1979_12
Patent number
US04177349

Reaction notes

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