Boron tribromide → HCID 178515147, compound

HRID 323649Notes

Reaction equation

HRID 323649 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178492078HCID 178492078, compound

Product 1

HCID 178515147HCID 178515147, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of the 7-chloro-4-hydroxy-2-(4′-methoxyphenyl)-5,10-dihydro-2H-pyridazino[4,5-b]quinoline-1-one (521 mg) in methylene chloride (50 mL), cooled in an ice/water bath, was added BBr3 dropwise (0.300 mL). The mixture was stirred with cooling for 15 minutes. The cooling bath was removed and the reaction was stirred at room temperature for 3 hours. The resulting solution was cooled to 0° C. and saturated NaHCO3 (55 mL) was added. The resulting mixture was stirred for 20 minutes, then the pH was adjusted with 6N HCl to pH=2. This was stirred for 15 minutes and the mixture was neutralized with saturated NaHCO3. The mixture was filtered and the paste residue was washed twice with ethyl acetate. The crude solid was taken in water (25 mL) and extracted three times with ethyl acetate/THF (4:1). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to dryness. The residue was triturated in ethyl acetate to afford the title compound as a yellow solid (48%). mp 210-212° C. (decomp.); MS 342(m+H); NMR 3.78(s,2H), 7.69(d,2H,J=8.8 Hz), 6.92(dd,1H,J1=8 Hz,J2=2 Hz), 7.10(d,1H,J=8 Hz), 7.20(d,1H,J=2 Hz), 7.26(d,2H,J=8.8 Hz), 9.0 (s,1H), 9.59(bs,1H), 1.95(bs,1H).

Workup

  1. temperaturecooled in an ice/water bath
  2. temperaturewith cooling for 15 minutes
  3. customThe cooling bath was removed
  4. stirringthe reaction was stirred at room temperature for 3 hours
  5. additionsaturated NaHCO3 (55 mL) was added
  6. stirringThe resulting mixture was stirred for 20 minutes
  7. stirringThis was stirred for 15 minutes
  8. filtrationThe mixture was filtered
  9. washthe paste residue was washed twice with ethyl acetate
  10. extractionextracted three times with ethyl acetate/THF (4:1)
  11. dry with materialThe organic phase was dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo to dryness
  14. customThe residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-dee28df66503455594a8913372d24b2a
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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