Hydrochloric Acid → HCID 23042373, compound

HRID 2165806Notes

Reaction equation

HRID 2165806 reaction equation
O.Cl.[Cl:3][C:4]1[CH:17]=[C:16]([F:18])[C:15]([N+:19]([O-])=O)=[CH:14][C:5]=1[C:6]([O:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]>C(O)C.[Fe]>[NH2:19][C:15]1[C:16]([F:18])=[CH:17][C:4]([Cl:3])=[C:5]([CH:14]=1)[C:6]([O:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 23042356Cyclopentyl 2-chloro-4-fluoro-5-nitrobenzoate

Product 1

HCID 23042373HCID 23042373, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

71 g of iron powder are placed in 190 ml of ethanol, 50 ml of water and 5 ml of 32% hydrochloric acid while stirring and the whole is heated to 75° C. (internal temperature). A warm solution of 100 g of cyclopentyl 2-chloro-4-fluoro-5-nitrobenzoate in 50 ml of ethanol is added dropwise to this mixture. The reaction mixture is stirred at 70°-75° C. (internal temperature) for a further 2 hours, cooled, after cooling suction filtered over Celite and the residue on the suction filter is rinsed with 500 ml of water followed by 200 ml of ethyl acetate. The filtrate is brought to a PH value of 8 with saturated potassium bicarbonate solution and the resulting brown precipitate is filtered off over Celite. The filtrate is extracted twice with 400 ml of ethyl acetate each time. the combined organic phases are washed twice with 200 ml of saturated sodium chloride solution each time, dried over anhydrous magnesium sulphate and concentrated. Then, the residue is purified by chromatography on a silica gel column using ethyl acetate/n-hexane (1:4) as the eluent and crystallized from diisopropyl ether/n-hexane. In this manner there is obtained cyclopentyl 5-amino-2-chloro-4-fluorobenzoate, m.p. 61°-62° C.

Workup

  1. temperaturecooled
  2. temperatureafter cooling suction
  3. filtrationfiltered over Celite
  4. filtrationthe residue on the suction filter
  5. washis rinsed with 500 ml of water
  6. filtrationthe resulting brown precipitate is filtered off over Celite
  7. extractionThe filtrate is extracted twice with 400 ml of ethyl acetate each time
  8. washthe combined organic phases are washed twice with 200 ml of saturated sodium chloride solution each time
  9. dry with materialdried over anhydrous magnesium sulphate
  10. concentrationconcentrated
  11. customThen, the residue is purified by chromatography on a silica gel column
  12. customcrystallized from diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-040795e056a7495b90963b1c9b3f5cc7
Source dataset
uspto-grants-1990_07
Patent number
US04941909

Reaction notes

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