Nitrogen → 2,2-dimethyl-N-(pyridin-3-yl)propanamide

HRID 1640904Notes

Reaction equation

HRID 1640904 reaction equation
N#N.[NH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20]>C(OCC)C.C1COCC1>[CH3:17][C:18]([CH3:23])([CH3:22])[C:19]([NH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:20]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 100093-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 46550442,2-dimethyl-N-(pyridin-3-yl)propanamideYield 76.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Equip a 250-mL round bottom flask with an ice bath, a magnetic stirrer, and a N2 atmosphere. Add 3-aminopyridine (15 g, 159 mmol), THF (60 mL), diethylether (60 mL), triethylamine (17.7 g, 24.4 mL, 175 mmol). Cool the mixture to 0° C. and add trimethylacetyl chloride (21.0 g, 14.9 mL, 175 mmol) slowly via syringe. Mix overnight while warming to RT. Add water (100 mL), transfer to a separatory funnel, and extract and discard the lower aqueous layer. Dry the organic layer over Na2SO4, filter, and concentrate via a rotovap to a colorless oil that solidifies on cooling. Dry under high vacuum for 2.5 h to give the title compound as a tan solid 21.56 g (76%). MS (ES) m/z 179 [M+1]+.

Workup

  1. customEquip a 250-mL round bottom flask with an ice bath, a magnetic stirrer
  2. additionMix overnight
  3. temperaturewhile warming to RT
  4. extractionAdd water (100 mL), transfer to a separatory funnel, and extract
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate via a rotovap to a colorless oil that
  8. temperatureon cooling
  9. customDry under high vacuum for 2.5 h

Sources & evidence

ORD record
ord-ca0666fd276447bb9d8e467bb35f1863
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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