Sodium Bicarbonate → HCID 57387082, compound

HRID 1800656Notes

Reaction equation

HRID 1800656 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])O.[Na+].[Cl:15][C:16]1[C:24]([C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>O1CCCC1>[Cl:15][C:16]1[C:24]([C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8])=[O:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 135191803-Amino-4-fluorophenolHCID 86646066HCID 86646066, compound

Product 1

HCID 57387082HCID 57387082, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A two-layer mixture of a solution of 3-amino-4-fluorophenol (9.00 g, 70.8 mmol) in tetrahydrofuran (50 mL) and aqueous sodium hydrogen carbonate (13.9 g, 166 mmol) solution (100 mL) was vigorously stirred, while adding dropwise a solution of 2-chloro-3-(1-cyanocyclopropyl)benzoyl chloride synthesized above in tetrahydrofuran (60 mL). The reaction mixture was stirred at room temperature for 1 hr. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from hexane/ethyl acetate (120 mL/40 mL) to give the title compound (23.4 g, 100%) as a brown powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hr
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
  4. washThe combined organic layer was washed with saturated brine (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was crystallized from hexane/ethyl acetate (120 mL/40 mL)

Sources & evidence

ORD record
ord-8b6c9596cb9c4a27919beb4380e79e7b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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