Nicotinic Acid → HCID 15680006, compound

HRID 359880Notes

Reaction equation

HRID 359880 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C([N:12]([CH2:15][CH3:16])CC)C.ClC(OCC)=O.N[C:24]1([OH:30])[CH2:29]CC[CH2:26][CH2:25]1>O1CCCC1>[OH:30][CH:24]1[CH2:29][CH2:16][CH:15]([NH:12][C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[O:9])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 147398371-Aminocyclohexan-1-ol

Product 1

HCID 15680006HCID 15680006, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-4 °C

Procedure

Nicotinic acid (2.14 g, 0.017 mol) was suspended in 75 mL of dry tetrahydrofuran, then 1.76 g of freshly distilled triethylamine were added. The clear solution thus obtained was cooled to -4° C. in an ice bath under argon, then ethyl chloroformate (1.88 g, 0.014 mol) in 10 mL of tetrahydrofuran was added such that the temperature did not go above 0° C. The free aminocyclohexanol (2.0 g, 0.017 mol) was added as a powder to the cold reaction mixture, which was allowed to come to room temperature and stirred for 2 hours. The precipitate which formed was collected by filtration, dissolved in 28 mL of hot water and recrystallized as 3.25 g (85%) of fine colorless needles melting at 208°-210° C. and having the formula ##STR113## as confirmed by elemental analysis.

Workup

  1. customThe clear solution thus obtained
  2. customdid not go above 0° C
  3. customto come to room temperature
  4. customThe precipitate which formed
  5. filtrationwas collected by filtration
  6. dissolutiondissolved in 28 mL of hot water
  7. customrecrystallized as 3.25 g (85%) of fine colorless needles melting at 208°-210° C.

Sources & evidence

ORD record
ord-7aa5e6d53855427999497fa1cf8004bc
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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