Nicotinic Acid → HCID 86673654, compound

HRID 1530185Notes

Reaction equation

HRID 1530185 reaction equation
[C:1](O)(=O)[C:2]1C=CC=[N:4][CH:3]=1.[C:10]1([CH3:17])C(C)=CC=C[CH:15]=1.[CH2:18]([NH2:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].[OH2:37]>>[CH2:21]([C:20]1[N:4]=[CH:3][CH:2]=[CH:1][C:19]=1[C:18]([NH2:36])=[O:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:15][CH2:10][CH3:17]

Participants

5

Reactant 4

HCID 938Nicotinic AcidHCID 962WaterHCID 7237O-Xylene2×HCID 5356789Oleylamine

Product 1

HCID 86673654HCID 86673654, compound

Conditions

Temperature
200 °C

Procedure

Nicotinic acid (75 g, 0.61 mmoles) and 10 mL of xylene were charged to a reactor that is equipped with a sub-surface nitrogen flow, a Dean-Stark trap filled with 25 mL of xylene, and a mechanical stirrer. Oleylamine (163.2 g, 0.61 moles) was added to this mixture dropwise. The mixture was heated to up to 200° C. and held until about 6 mL of water collected in the Dean-Stark trap. The temperature was reduced to about 120° C. and the mixture was then vacuum stripped to provide a dark residue that had a TBN of 168.6 by D2896 method and had infra-red bands at 3300.7, 1626.4, 1545.5, and 707.6 cm−1.

Workup

  1. customis equipped with a sub-surface nitrogen flow
  2. customcollected in the Dean-Stark trap
  3. customwas reduced to about 120° C.
  4. customto provide a dark residue that

Sources & evidence

ORD record
ord-fa5aca3a0ba0448a88aac29b50c5b8ee
Source dataset
uspto-grants-2015_07
Patent number
US09090847B2

Reaction notes

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