Sulfuric Acid → Quinoline, 7,8-Difluoro-

HRID 2241981Notes

Reaction equation

HRID 2241981 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Na+].[N+]([C:14]1[CH:15]=C(S([O-])(=O)=O)C=C[CH:19]=1)([O-])=O.OS(O)(=O)=O.[OH-].[Na+]>OCC(CO)O>[F:9][C:8]1[C:2]([F:1])=[C:3]2[C:5]([CH:19]=[CH:14][CH:15]=[N:4]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 782782,3-Difluoroaniline

Product 1

HCID 3025799Quinoline, 7,8-Difluoro-

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
135 °C

Procedure

To a mixture of 2,3-difluoroaniline (commercially available, 3.57 g), glycerol (5.55 g) and m-nitrobenzene sulfonic acid sodium salt (10.12 g) was added dropwise 70% H2SO4 (20 mL). The reaction was heated at 135° C. for 3.5 hours and then cooled to room temperature. It was poured over ice, made basic with 50% aqueous NaOH and extracted with Et2O. The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated on a rotary evaporator to give 4.13 g of the desired product as a light brown solid; MS (ES) m/z (relative intensity); 166 (M+H)+ (100).

Workup

  1. temperaturecooled to room temperature
  2. additionIt was poured over ice
  3. extractionextracted with Et2O
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-d5a99f18c22f48e68127b3f47a52659a
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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