Hydrochloric Acid → 2-Amino-3-nitro-6-(2,2,2-trifluoro-ethoxy)-benzoic acid ethyl ester

HRID 18615

Reaction equation

[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[CH2:9]([O:11][C:12](=[O:24])[C:13]1[C:18](F)=[CH:17][CH:16]=[C:15]([N+:20]([O-:22])=[O:21])[C:14]=1[NH2:23])[CH3:10].Cl>C1COCC1>[CH2:9]([O:11][C:12](=[O:24])[C:13]1[C:18]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])=[CH:17][CH:16]=[C:15]([N+:20]([O-:22])=[O:21])[C:14]=1[NH2:23])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

420 mg NaH (60% suspension in oil) were added to a solution of 2.16 mL (29.8 mmol) 2,2,2-trifluoro-ethanol in 5 mL THF. When the gas evolution ceased, 1.0 g (4.38 mmol) 2-Amino-6-fluoro-3-nitro-benzoic acid ethyl ester was added. The resulting mixture was stirred at 0° C. for 30 minutes and at room temperature for further 30 minutes. To this mixture were added 2 mL of a 6 M aqueous HCl-solution, and most of the solvent was removed under reduced pressure. The residue was mixed with 20 mL water and the resulting solid was collected and washed with water and then hexane. The obtained yellow crystalline material was dried under reduced pressure at 35° C. Yield: 1.22 g.

Workup

custommost of the solvent was removed under reduced pressure
additionThe residue was mixed with 20 mL water
customthe resulting solid was collected
washwashed with water
customThe obtained yellow crystalline material was dried under reduced pressure at 35° C

Sources & evidence

ORD record: ord-72e6377cac6543abae76d361f020c377
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741341B2

Linked notes

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