Trifluoroacetic acid → HCID 66990423, compound

HRID 454523Notes

Reaction equation

HRID 454523 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([CH2:35][CH3:36])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=1)=O)(C)(C)C>C(Cl)Cl>[CH2:35]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=1)[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66990075HCID 66990075, compound

Product 1

HCID 66990423HCID 66990423, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.5 mL) was added to a methylene chloride (2.0 mL) solution of methyl 4-(2-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-nitrobenzoate (0.39 g) at room temperature, followed by stirring at the same temperature for 1 hour. The solvent was evaporated under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate] to obtain 0.27 g of methyl 4-(2-(ethylamino)phenyl)-2-nitrobenzoate as an orange oily substance.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  2. additiona saturated aqueous solution of sodium bicarbonate were added to the residue
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-7c5ba6a663f6421297a3a0655a9fb48b
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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