Triethylamine → HCID 14773914, compound

HRID 329766Notes

Reaction equation

HRID 329766 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15].C(N(CC)CC)C>C(O)(C)C>[OH:16][CH:13]([CH2:14][OH:15])[CH2:12][NH:11][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 14773914HCID 14773914, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (3.22 g, 20.3 mmol), 3-amino-1,2-propanediol (1.85 g, 20.3 mmol) and triethylamine (2.05 g, 20.3 mmol) in isopropanol (80 mL) was stirred at 20°-25° C. for 18 hours and then at reflux for 6 hours. After concentrating under reduced pressure, the residue was flash chromatographed over silica gel. Elution with 5% MeOH-95% CHCl3 and recrystallization from EtOAc-hexane afforded analytically pure product (2.64 g, 61%), m.p. 95.5°-98.0° C.

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationAfter concentrating under reduced pressure
  3. customchromatographed over silica gel
  4. washElution
  5. customwith 5% MeOH-95% CHCl3 and recrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-00ae4c1130c44f8c98f608072ca0446a
Source dataset
uspto-grants-1990_01
Patent number
US04892951

Reaction notes

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