Sodium amide → 6-(Pentan-3-yl)pyridin-2-amine

HRID 359911Notes

Reaction equation

HRID 359911 reaction equation
[NH2-:1].[Na+].C(O)(=O)CCCCCCC/C=C\CCCCCCCC.[CH3:23][CH2:24][CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH2:26][CH3:27].[H][H]>O.C1(C)C(C)=CC=CC=1>[NH2:1][C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([CH:25]([CH2:26][CH3:27])[CH2:24][CH3:23])[N:29]=1

Participants

7

Reactant 4

HCID 24533Sodium amideHCID 818872-(1-Ethylpropyl)pyridineHCID 445639Oleic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 200643446-(Pentan-3-yl)pyridin-2-amineYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 105.8 g (2.71 moles) of sodamide and 332 g of xylene containing 1.0 cc of oleic acid was placed in a liter Magne Drive, equipped as described in Example 15. The autoclave was closed and purged of air with nitrogen and pressurized to 100 psig with nitrogen. The pressure relief valve was set at 100 psig. Cooling water was turned on the reflux condenser. The mixture was heated with stirring to 190° C. and 235.0 g (1.58 moles) of 2-(3-pentyl)pyridine was started adding from a Fisher-porter pressure bottle. The addition required 5.5 hours at 190° C.-215° C. The reaction mixture was heated an additional 5 hours within that temperature range until hydrogen almost stopped passing through the relief valve. The autoclave was cooled to 50° C., vented to atmospheric pressure and hydrolyzed with 200 cc of water. The oil layer was separated and distilled under vacuum to give 258.6 g of 2 -amino-6-(3-pentyl)pyridine. b.p. 163° C. at 60 mm. n25D 1.5357 (yield 68.1%). This 2-amino-6-pentyl)pyridine is a new composition of matter. It is a novel liquid aminopyridine and has valuable biocidal properties. When this amination is repeated at atmospheric pressure under classic Chichibabin conditions, the product is 6,6'-di-(3-pentyl)-2,2'-bipyridyl as shown in McGill, U.S. Pat. No. 4,177,349 (1979) and McGill, U.S. Pat. No. 4,267,335 (1981).

Workup

  1. customequipped
  2. customThe autoclave was closed
  3. custompurged of air with nitrogen
  4. temperatureThe mixture was heated
  5. additionThe addition required 5.5 hours at 190° C.-215° C
  6. temperatureThe autoclave was cooled to 50° C.
  7. customThe oil layer was separated
  8. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-45630c48342b446cb2eb7313d60d396b
Source dataset
uspto-grants-1991_03
Patent number
US05003069

Reaction notes

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