Hydrochloric Acid → 2,2-difluoro-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-quinoline]

HRID 551830Notes

Reaction equation

HRID 551830 reaction equation
[F:1][C:2]1([F:22])[C:4]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7](NC(OC(C)(C)C)=O)[CH2:6][CH2:5]2)[CH2:3]1.Cl>ClCCl.O1CCOCC1>[F:22][C:2]1([F:1])[C:4]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH2:6][CH2:5]2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67192015tert-butyl 2,2-difluoro-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-quinoline]-1'-carbamate

Product 1

HCID 671885982,2-difluoro-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-quinoline]Yield 890.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.105 g of tert-butyl 2,2-difluoro-2′,3′-dihydro-1′H-spiro[cyclopropane-1,4′-quinoline]-1′-carbamate is dissolved in 5 ml of dichloromethane and then 7.78 ml of a 4N solution of hydrochloric acid in dioxane are added. Stirring is maintained for 14 hours. After evaporating, the residue is taken up in dichloromethane and then hydrolyzed with a saturated solution of sodium hydrogencarbonate in water. The mixture is extracted twice with dichloromethane. The organic phases are combined, washed with water and then with a saturated solution of sodium hydrogencarbonate in water and then dried over magnesium sulfate and the solvent is evaporated under reduced pressure. 0.588 g of 2,2-difluoro-2′,3′-dihydro-1′H-spiro[cyclopropane-1,4′-quinoline] is obtained.

Workup

  1. temperatureis maintained for 14 hours
  2. customAfter evaporating
  3. extractionThe mixture is extracted twice with dichloromethane
  4. washwashed with water
  5. dry with materialwith a saturated solution of sodium hydrogencarbonate in water and then dried over magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-dfa71f3a240040edae4abdcdfda9641e
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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