Phosphorus oxychloride → Ethyl 8-bromo-4-chloroquinoline-3-carboxylate

HRID 1469737Notes

Reaction equation

HRID 1469737 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]2O.O=P(Cl)(Cl)[Cl:20]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]2[Cl:20]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469454Ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 3418677Ethyl 8-bromo-4-chloroquinoline-3-carboxylate

Procedure

A solution of ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate (2.0 g, 6.75 mmol) in POCl3 (10 mL) was heated at 80° C. for 3 h. Then the volatiles were removed and ice-water was added to the residue. The precipitated solid was filtered and dried to afford 1.8 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 9.26 (s, 1H), 8.44-8.37 (m, 2H), 7.79-7.64 (t, J=7.8 Hz, 1H), 4.48-4.43 (q, J=7.2, 14.1 Hz, 2H), 1.41-1.36 (t, J=6.9 Hz, 3H); MS (m/z): 314.01 (M+H)+.

Workup

  1. customThen the volatiles were removed
  2. additionice-water was added to the residue
  3. filtrationThe precipitated solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-ec198745010749399569136b7dab2044
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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