Potassium Carbonate → HCID 178513321, compound

HRID 2172688Notes

Reaction equation

HRID 2172688 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2].[NH2:13][OH:14].Cl.C([O-])([O-])=O.[K+].[K+]>CCO.O>[F:12][C:5]1[CH:4]=[C:3]([C:1](=[NH:2])[NH:13][OH:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 5906594-Cyano-2-fluorobenzoic acid

Product 1

HCID 178513321HCID 178513321, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4-Cyano-2-fluorobenzoic acid (1 g, 6.06 mmol) in EtOH (10.09 mL) was added NH2OH.HCl (0.884 g, 12.72 mmol) previously dissolved in water (5 mL) and aqueous solution K2CO3 (1.339 g, 9.69 mmol) in water (15 mL). Then 8-hydroxyquinone (0.011 g, 0.079 mmol) was added. The resulting solution was stirred at reflux for 4 h. EtOH was evaporated from the reaction mixture, then acidified to pH 3 with aqueous HCl (2 N) solution. The precipitate was filtered, washed with water and dried to yield 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid (786.3 mg, 3.89 mmol, 64.2% yield) as yellowish solid. The crude was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm: 13.21 (m, 1 H), 10.01 (s, 1 H), 7.85 (t, J=7.95 Hz, 1 H), 7.44-7.69 (m, 2 H), 5.99 (br. s., 2 H).

Workup

  1. temperatureat reflux for 4 h
  2. customEtOH was evaporated from the reaction mixture
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-017e204d085d483c89088afde3edee5d
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

Loading…