Acetic Acid → HCID 25054598, compound

HRID 511776Notes

Reaction equation

HRID 511776 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[N+:15]([O-])=O)[CH:2]1[O:4][CH2:3]1.C(O)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>[Fe].CCO.O>[OH:4][CH2:3][CH:2]1[NH:15][C:7]2[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][C:6]=2[O:5][CH2:1]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 3190092-[(2,4-dinitrophenoxy)methyl]oxirane

Product 1

HCID 25054598HCID 25054598, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron powder (0.670 g, 12 mmol) was added into EtOH/H2O (v/v=6:1, 100 mL) solution of 2,4-dinitrophenyl glycidyl ether (0.480 g, 2 mmol) and acetic acid (1 mL, 17.5 mmol) at reflux temperature. The reaction mixture was refluxed continuously for 120 minutes, and cooled to room temperature, saturated Na2CO3 solution was used for adjusting pH=8, the solution was leached out with C salt for concentrating ethanol and water in the filtrate, and the solid ethanol was obtained (10 mL×4). Ethanol phase was dried with anhydrous MgSO4 and filtered to obtain crude products; the above crude products were separated with silica gel column chromatography (ethanol as developing agent), and 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine (0.149 g, 42%) was prepared.

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture was refluxed continuously for 120 minutes
  3. concentrationfor concentrating ethanol and water in the filtrate
  4. customthe solid ethanol was obtained (10 mL×4)
  5. dry with materialEthanol phase was dried with anhydrous MgSO4
  6. filtrationfiltered
  7. customto obtain crude products
  8. customthe above crude products were separated with silica gel column chromatography (ethanol as developing agent), and 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine (0.149 g, 42%)
  9. customwas prepared

Sources & evidence

ORD record
ord-58690b5cfa074b179e41351a21c9a7e1
Source dataset
uspto-grants-2015_08
Patent number
US09101634B2

Reaction notes

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