Nicotinic Acid → HCID 13773415, compound

HRID 1530184Notes

Reaction equation

HRID 1530184 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].[C:10](O)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1>>[C:10]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 938Nicotinic AcidHCID 77202-Ethylhexanol

Product 1

HCID 13773415HCID 13773415, compound

Conditions

Temperature
200 °C

Procedure

2-Ethylhexyl alcohol (215.5 g, 1.65 mol) was charged to a 500 ml resin kettle and equipped with mechanical stir, a Dean-Stark trap and a thermocouple. The mixture was stirred at 300 rpm and nicotinic acid (61.5 g, 0.5 mol) was added in portions through a powder funnel. The mixture was heated to 200° C. with sub-surface nitrogen flow and held for 6 hours. The mixture was then cooled to 150° C. and vacuum was applied to −15 in Hg and held for 45 min. 22.9 g process oil was added and the mixture was then allowed to cool to room temperature under nitrogen atmosphere. The resulting mixture was then filtered twice through Celite Hyflow and Whatman #1 filter paper to yield desired product.

Workup

  1. customequipped with mechanical stir
  2. additionwas added in portions through a powder funnel
  3. temperatureThe mixture was then cooled to 150° C.
  4. waitheld for 45 min
  5. addition22.9 g process oil was added
  6. temperatureto cool to room temperature under nitrogen atmosphere
  7. filtrationThe resulting mixture was then filtered twice through Celite Hyflow and Whatman #1
  8. filtrationfilter paper

Sources & evidence

ORD record
ord-74ffc68c59ee47c2b6d2e4f083396072
Source dataset
uspto-grants-2015_07
Patent number
US09090847B2

Reaction notes

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