Phosphorus oxychloride → 7-Bromo-4-chloro-3-nitroquinoline

HRID 909334Notes

Reaction equation

HRID 909334 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:18]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:18])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418737HCID 178418737, compound

Product 1

HCID 219843617-Bromo-4-chloro-3-nitroquinoline

Procedure

7-Bromo-3-nitroquinolin-4-ol (42 g, 156 millimoles (mmol)) was suspended in POCl3 (130 mL) and brought to 102° C. under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature (RT). The resulting solids were collected by filtration, washed with H2O, and then partitioned with CH2Cl2 (3 L) and 2M Na2CO3 (500 mL). The organic layer was separated, washed with H2O (1×), dried over Na2SO4, filtered, and concentrated to afford 33.7 g of 7-bromo-4-chloro-3-nitroquinoline as a beige solid.

Workup

  1. custombrought to 102° C. under an atmosphere of N2
  2. dissolutionall of the solids had dissolved, so the reaction
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with H2O
  5. custompartitioned with CH2Cl2 (3 L) and 2M Na2CO3 (500 mL)
  6. customThe organic layer was separated
  7. washwashed with H2O (1×)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-68d6770081364880b85d0d45b3b5d10c
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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