Hydrochloric Acid → 4-Difluoromethylene-1,2,3,4-tetrahydroquinoline

HRID 551822Notes

Reaction equation

HRID 551822 reaction equation
[F:1][C:2]([F:21])=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6](NC(OC(C)(C)C)=O)[CH2:5][CH2:4]1.Cl>ClCCl.O1CCOCC1>[F:21][C:2]([F:1])=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67188534tert-butyl 4-difluoromethylene-3,4-dihydro-2H-quinoline-1-carbamate

Product 1

HCID 671881714-Difluoromethylene-1,2,3,4-tetrahydroquinolineYield 104.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.11 g of tert-butyl 4-difluoromethylene-3,4-dihydro-2H-quinoline-1-carbamate in 10 ml of dichloromethane is introduced into a round-bottomed flask equipped with a magnetic stirrer. 6 ml of a 4N solution of hydrochloric acid in dioxane are added. After stirring at ambient temperature for 6 h, the reaction medium is concentrated under vacuum. 0.07 g of 4-difluoromethylene-1,2,3,4-tetrahydroquinoline is obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. concentrationthe reaction medium is concentrated under vacuum

Sources & evidence

ORD record
ord-c8c833fb7b7c40809e09c89c00275c69
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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