Sulfuric Acid → HCID 178496976, compound

HRID 500571Notes

Reaction equation

HRID 500571 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[F:23].OS(O)(=O)=O.[N:30]([O-])=O.[Na+]>C1COCC1.O.CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[F:23])[N:13]=[N:30][CH:11]=[C:10]2[OH:12])=[O:24]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 86598641HCID 86598641, compound

Product 1

HCID 178496976HCID 178496976, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-acetyl-4-amino-2-(4-bromo-2-fluorophenylamino)-3-fluorobenzoic acid methyl ester (1.00 equiv.) in THF and conc H2SO4 (4.00 equiv.) is added a solution of NaNO2 (1.50 equiv.) in water at 0° C. The reaction mixture is warmed to 60° C. and stirred for 3 hours. The reaction mixture is cooled to room temperature and diluted with EtOAc. The organic layer is washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give the crude material that is purified by flash column chromatography to afford the desired product as necessary.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washThe organic layer is washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude material that
  7. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-544e33badc6f45b1a34270ffef797715
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

Loading…