Phosphorus oxychloride → 4-Chlorofuro[3,2-c]pyridine

HRID 734304Notes

Reaction equation

HRID 734304 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][NH:6][C:5](=O)[C:4]=2[CH:3]=[CH:2]1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:5]1[C:4]2[CH:3]=[CH:2][O:1][C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2887464H,5H-furo(3,2-c)pyridin-4-one

Product 1

HCID 27797464-Chlorofuro[3,2-c]pyridine

Conditions

Temperature
120 °C

Procedure

5H-Furo[3,2-c]pyridin-4-one (5.9 g) was suspended with POCl3 (12 ml) and the reaction mixture was stirred for 3 hours at 120° C. After evaporating POCl3, crushed ice was added and poured into the mixture of ethyl acetate and saturated NaHCO3. The corresponding organic phase was separated and dried over Na2SO4 and then concentrated in vacuo. The resultant residue was purified by chromatography on a silica gel column to afford 4-chloro-furo[3,2-c]pyridine (5.6 g) 1H NMR (400 MHz, DMSO-d6) ppm 8.31 (d, J=5.8 Hz, 1H), 8.26 (d, J=2.3 Hz, 1H), 7.79 (dd, J=1.0, 5.6 Hz, 1H), 7.13 (dd, J=1.0, 2.3 Hz, 1H).

Workup

  1. customAfter evaporating POCl3
  2. customcrushed ice
  3. additionwas added
  4. additionpoured into the mixture of ethyl acetate and saturated NaHCO3
  5. customThe corresponding organic phase was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-377f58a934af4b66ba688830e164e264
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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