Hydrochloric Acid → HCID 14256908, compound

HRID 2081146Notes

Reaction equation

HRID 2081146 reaction equation
O.Cl.[Cl:3][C:4]1[CH:20]=[C:19]([F:21])[C:18]([N+:22]([O-])=O)=[CH:17][C:5]=1[C:6]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7]>C(O)C.[Fe]>[NH2:22][C:18]1[C:19]([F:21])=[CH:20][C:4]([Cl:3])=[C:5]([CH:17]=1)[C:6]([O:8][C:9]([CH3:15])([CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19780806HCID 19780806, compound

Product 1

HCID 14256908HCID 14256908, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 10 g of finely powdered iron. 50 ml of ethanol, 11 ml of water and 1 ml of concentrated hydrochloric acid is heated to 65° C. while stirring. To this mixture is added dropwise during 2 hours a solution of 15 g of ethyl 2-(2-chloro-4-fluoro-5-nitro-benzoyloxy)-2-methyl-propionate in 15 ml of ethanol in such a manner that the temperature does not rise above 80° C. After completion of the addition the reaction mixture is stirred at 70° C. for a further 16 hours. After cooling the reaction mixture is suction filtered over Celite®. The Celite® is rinsed well with water and with ethyl acetate. The filtrate is adjusted to pH 8 with 2N potassium bicarbonate solution. It is once more filtered over Celite® and again rinsed with water and ethyl acetate. The filtrate is now extracted three times with 400 ml of ethyl acetate each time. The organic phases are back-washed twice with 300 ml of saturated sodium chloride solution each time, dried over anhydrous magnesium sulphate and evaporated under reduced pressure. The residue is fractionated in a high vacuum and distilled. In this manner there is obtained ethyl 2-(5-amino-2-chloro-4-fluoro-benzoyloxy)-2-methylpropionate, b.p. 146°-151° C./0.07 torr.

Workup

  1. customdoes not rise above 80° C
  2. additionAfter completion of the addition the reaction mixture
  3. stirringis stirred at 70° C. for a further 16 hours
  4. temperatureAfter cooling the reaction mixture
  5. filtrationfiltered over Celite®
  6. washThe Celite® is rinsed well with water and with ethyl acetate
  7. filtrationIt is once more filtered over Celite®
  8. washagain rinsed with water and ethyl acetate
  9. extractionThe filtrate is now extracted three times with 400 ml of ethyl acetate each time
  10. washThe organic phases are back-washed twice with 300 ml of saturated sodium chloride solution each time
  11. dry with materialdried over anhydrous magnesium sulphate
  12. customevaporated under reduced pressure
  13. distillationdistilled

Sources & evidence

ORD record
ord-36680f399f7848e6b1218137ddd3abe9
Source dataset
uspto-grants-1993_02
Patent number
US05183492

Reaction notes

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