Ethanol → HCID 117843537, compound

HRID 2209041Notes

Reaction equation

HRID 2209041 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[C:14]([N+:19]([O-])=O)[C:10]=1[NH:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](O)C>C(O)=O.[Fe]>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH2:12][CH3:13])[CH:22]=[N:19][C:14]=2[CH:15]=[C:16]([Br:18])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 117843323HCID 117843323, compound

Product 1

HCID 117843537HCID 117843537, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(benzyloxy)-4-bromo-N-ethyl-6-nitroaniline (230 mg, 0.66 mmol) in ethanol (10 mL) and formic acid (10 mL) was added iron (731 mg, 13.1 mmol) and the reaction mixture was heated at 90° C. at 2 h. The reaction mixture was concentrated, diluted with water and brought to pH ˜7 with sat′d NaHCO3 and then the aqueous layer was extracted with EtOAc (3×). Combined organic layer was then washed successively with water and brine and dried over anhydrous magnesium sulfate, filtered, evaporated, and dried to give the title compound which was used further without purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C16H16BrN2O: 331.0; found: 331.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionthe aqueous layer was extracted with EtOAc (3×)
  4. washCombined organic layer was then washed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customdried

Sources & evidence

ORD record
ord-e56865cc8f424986abc025e6700a94e9
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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