3-Amino-1-propanol → HCID 61206961, compound

HRID 2112394Notes

Reaction equation

HRID 2112394 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:11])O[C:9](=[O:10])[C:2]=12.[NH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C(Cl)(Cl)Cl>[OH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:7](=[O:11])[C:3]2[C:2](=[N:1][CH:6]=[CH:5][CH:4]=2)[C:9]1=[O:10]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 69688Furo[3,4-b]pyridine-5,7-dione

Product 1

HCID 61206961HCID 61206961, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
155 °C

Procedure

To a suspension of 4.0 g (27 mmol) furo[3,4-b]pyridine-5,7-dione in 10 ml chloroform a solution of 2.03 g (27 mmol) of 3-aminopropanol in 7 ml chloroform was added and the mixture was heated to reflux for 30 minutes. Now the solvent was slowly evaporated and the mixture was gradually heated to 150-160° C. while the vacuum was maintained. After two hours the mixture was cooled to room temperature and the brownish crude product was purified by flash chromatography (silica gel, ethyl acetate/MeOH 15:1) to afford 3.9 g (70%) of the desired product as a white powder. 1H-NMR (CDCl3): 1.89-1.95 (m, 2H), 2.25 (s, br, 1H), 3.64-3.68 (m, 2H), 3.90-3.96 (m, 2H), 7.60-7.66 (m, 1H), 8.14-8.20 (m, 1H), 8.93-8.99 (m, 1H).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 30 minutes
  4. customNow the solvent was slowly evaporated
  5. temperaturewas maintained
  6. temperatureAfter two hours the mixture was cooled to room temperature
  7. customthe brownish crude product was purified by flash chromatography (silica gel, ethyl acetate/MeOH 15:1)

Sources & evidence

ORD record
ord-bb5dd2b64c174886b6fceda4cb0b5904
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

Loading…