Trifluoroacetic acid → Methyl (4-formyl-3-nitrophenyl)carbamate

HRID 1481275Notes

Reaction equation

HRID 1481275 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:16])[O:14][CH3:15])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18].C(O)(C(F)(F)F)=O>O>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:16])[O:14][CH3:15])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18])=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71263042Methyl (4-(1,3-dioxolan-2-yl)-3-nitrophenyl)carbamate

Product 1

HCID 89410473Methyl (4-formyl-3-nitrophenyl)carbamateYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5C (5.00 g, 18.64 mmol) was added to a solution of TFA (27 mL) and H2O (3 mL) and stirred at rt for 3 h. After 3 h, the reaction mixture was concentrated and the residue was partitioned between H2O and EtOAc. The organic layer was then washed with saturated sodium bicarbonate solution followed by brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated to give a light yellow solid as 5D (3.83 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 10.09 (s, 1H), 8.23 (d, J=1.6 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.86-7.81 (m, 1H), 3.74 (s, 3H) ppm.

Workup

  1. waitAfter 3 h
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was partitioned between H2O and EtOAc
  4. washThe organic layer was then washed with saturated sodium bicarbonate solution
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3a139e41ecd549b59d2b5428669133ef
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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