Sodium Bicarbonate → HCID 4456250, compound

HRID 1994112Notes

Reaction equation

HRID 1994112 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH:14]C(=O)C)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>Br.CCOC(C)=O>[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH2:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 24824867HCID 24824867, compound

Product 1

HCID 4456250HCID 4456250, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

N-(2-tert-butyl-4-nitrophenyl)acetamide (840 mg, 3.57 mmol) was dissolved in concentrated HBr (48%, 20 mL). The resulting solution was heated at 110° C. for 3 h. The reaction mixture was cooled to rt, diluted with EtOAc, and poured into sat. NaHCO3 solution. The organic phase was extracted with sat. NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated to give the desired product as a yellow-green oil (710 mg, >100%). 1H NMR (400 MHz, CD3OD) δ: 7.52 (d, 1H), 7.40 (dd, 1H), 7.33 (d, 1H), and 1.42 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe organic phase was extracted with sat. NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66711da6d3a1424386311957de18e4b8
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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