1-Butanol → HCID 86662395, compound

HRID 389419Notes

Reaction equation

HRID 389419 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12.C(O)CCC.Cl.[CH3:17][O:18][NH2:19]>O>[CH3:17][O:18][NH:19][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12

Participants

5

Reactant 3

HCID 2631-ButanolHCID 521874O-Methylhydroxylamine hydrochloride2×HCID 128261077-Chlorofuro[2,3-c]pyridine

Product 1

HCID 86662395HCID 86662395, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A three-necked flask was charged with 7-chloro-furo[2,3-c]pyridine (40 g, 0.26 mol) and n-butanol (300 mL) and heated at 125° C. Methoxyamine hydrochloride (54 g, 0.65 mol) was added as a solid and then additional methoxyamine hydrochloride (54 g, 0.65 mol) dissolved in water (50 mL) was added slowly. The resulting mixture was heated at reflux overnight. After cooling to RT, the reaction mixture was concentrated in vacuo. The remaining aqueous solution was basified to pH ˜8.5 with saturated NaHCO3 and extracted several times with DCM. The combined DCM extracts were washed with saturated NaHCO3 and brine. This solution was concentrated in vacuo leaving a dark brown syrup which was used without further purification.

Workup

  1. additionwas added slowly
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux overnight
  4. temperatureAfter cooling to RT
  5. concentrationthe reaction mixture was concentrated in vacuo
  6. extractionextracted several times with DCM
  7. washThe combined DCM extracts were washed with saturated NaHCO3 and brine
  8. concentrationThis solution was concentrated in vacuo
  9. customleaving a dark brown syrup which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-166bc5e8f0434d499b09f12cfe1d5824
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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