Ethanolamine → HCID 59596532, compound

HRID 2264913Notes

Reaction equation

HRID 2264913 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.CO>C(O)(C)C>[OH:2][CH2:1][CH2:3][NH:4][C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 887MethanolHCID 81531DiisopropylethylamineHCID 134111124-Chloro-nicotinonitrile

Product 1

HCID 59596532HCID 59596532, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethanolamine (0.60 mL, 10.0 mmol), 4-chloronicotinonitrile (1.38 g, 10.0 mmol) and diisopropylethylamine (1.74 mL, 10.0 mmol) in isopropanol was heated at reflux for 2.5 hours. It was cooled to room temperature and loaded on to a 50 g SCX-2 cartridge preconditioned with methanol. The cartridge was eluted with methanol and then with a 2M solution of ammonia in methanol. Collecting appropriate fractions followed by evaporation of solvents gave the title compound as a beige solid (1.20 g, 74%). 1H NMR (d6-DMSO, 400 MHz) 8.40 (s, 1H), 8.21 (d, J=6.3 Hz, 1H), 6.94 (bs, 1H), 6.77 (d, J=6.3 Hz, 1H), 4.84 (bs, 1H), 3.55 (t, J=6.0 Hz, 2H), 3.31 (dt, J=6.0 Hz, 6.0 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. washThe cartridge was eluted with methanol
  4. customCollecting appropriate fractions
  5. customfollowed by evaporation of solvents

Sources & evidence

ORD record
ord-286e4b3630f34b8a96c972b56a27b03e
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

Loading…