Phosphorus trichloride → 2-Chloroquinoline

HRID 2417164Notes

Reaction equation

HRID 2417164 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[N+]([O-])=O.P(Cl)(Cl)[Cl:16]>>[Cl:16][C:3]1[CH:2]=[CH:11][C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:4]=1

Participants

3

Reactant 2

HCID 24387Phosphorus trichlorideHCID 226338743-Nitroisoquinolin-4-ol

Product 1

HCID 119282-ChloroquinolineYield 42.5%

Procedure

To 13.25 g (69.7 mmol) of 4-hydroxy-3-nitroisoquinoline was added 120 mL of phosphorous trichloride. After the mixture had been refluxed for 3 hours, 80 mL of POCl3 was distilled out. The remaining solution was poured onto approximately 150 g of crushed ice. The resulting solid was filtered and recrystallized from ethanol to give 6.2 g (42.5%) of the chioroquinoline as yellow needles: mp 103-104° C. (lit mp 108-109° C.); 1H-NMR (DMSO-d6, 200 MHz) δ 9.20 (s, 1H), 8.5 (d, 1H) 8.30 (d, 1H), 7.8 (m, 2H); IR (KBr) 1530 (s, NO2), 1344 (s, NO2) cm−1.

Workup

  1. temperatureAfter the mixture had been refluxed for 3 hours
  2. distillation80 mL of POCl3 was distilled out
  3. additionThe remaining solution was poured onto approximately 150 g of crushed ice
  4. filtrationThe resulting solid was filtered
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0ef5867e0f0f4d8ab255d2694753947b
Source dataset
uspto-grants-2004_11
Patent number
US06825347B2

Reaction notes

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