Methanol → HCID 28373819, compound

HRID 714575Notes

Reaction equation

HRID 714575 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[Cl:15].C1COCC1.CO>C(O)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[Cl:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 86694551HCID 86694551, compound

Product 1

HCID 28373819HCID 28373819, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a three-neck flask (500 ml) was added 1-(2-chlorobenzyloxy)-2-chloro-4-nitrobenzene (8.567 g). To the flask were added THF (100 ml) and methanol (50 ml). The solution was mechanically stirred and heated under reflux. Glacial acetic acid (17 ml) and reduced iron powders (16.8 g) were added into the solution. The mixture reacted for 1 hr. After the reaction finished, the resultant substance was filtered in vacuo and the filtrate was rotary-evaporated to dryness. To the resultant crude product was added HCl (4N, 200 ml). The mixture was sufficiently vibrated and then filtered in vacuo. To the resultant filter cake was added water (100 ml). The pH of the mixture was adjusted to 12 with 5% sodium hydroxide. Ethyl acetate (700 ml) was added. The solution was sufficiently vibrated and separated. The ethyl acetate layer was washed with saturated sodium carbonate (200 ml), water (200 ml) and staturated saline solution (200 ml), successively. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was rotary-evaporated to dryness. The resultant substance was recrystallized with ethyl acetate to give the target compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe mixture reacted for 1 hr
  4. filtrationthe resultant substance was filtered in vacuo
  5. customthe filtrate was rotary-evaporated to dryness
  6. additionTo the resultant crude product was added HCl (4N, 200 ml)
  7. filtrationfiltered in vacuo
  8. filtrationTo the resultant filter cake
  9. additionwas added water (100 ml)
  10. additionEthyl acetate (700 ml) was added
  11. customseparated
  12. washThe ethyl acetate layer was washed with saturated sodium carbonate (200 ml), water (200 ml)
  13. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. customThe solvent was rotary-evaporated to dryness
  16. customThe resultant substance was recrystallized with ethyl acetate
  17. customto give the target compound

Sources & evidence

ORD record
ord-d2ca08e8045a4e888249b09d2f6e149b
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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