Sodium Hydroxide → 4-Bromo-3-(3,4-difluoro-benzenesulfonyl)-7-nitro-quinoline

HRID 561048Notes

Reaction equation

HRID 561048 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2O)=[CH:19][CH:18]=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=3)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].O(Br)[Br:27].[P+5].[OH-].[Na+]>CN(C=O)C.O>[Br:27][C:21]1[C:20]2[C:15](=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[S:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 178419731HCID 178419731, compoundHCID 178526461HCID 178526461, compound

Product 1

HCID 670003164-Bromo-3-(3,4-difluoro-benzenesulfonyl)-7-nitro-quinolineYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(3,4-difluoro-benzenesulfonyl)-7-nitro-quinolin-4-ol (1.6 g, 4.37 mmol) and phosphorus(V) oxybromide (2.5 g, 8.72 mmol) in DMF (16 ml) was stirred at 65° C. for 1 hour. The reaction mixture was diluted with water (100 ml) and the pH was adjusted to 10 with aqueous sodium hydroxide solution. After cooling the precipitate was filtered and washed with water. The obtained crude product was purified by crystallization from ethanol to obtain 1.25 g of the title compound in 67% yield.

Workup

  1. temperatureAfter cooling the precipitate
  2. filtrationwas filtered
  3. washwashed with water
  4. customThe obtained crude product
  5. customwas purified by crystallization from ethanol

Sources & evidence

ORD record
ord-6e96b4f74ea14075a39bcc6d2c4beeb0
Source dataset
uspto-grants-2011_11
Patent number
US08063220B2

Reaction notes

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