Cyclopropylamine → 1,8-Diazabicyclo(5.4.0)undec-7-ene

HRID 981189Notes

Reaction equation

HRID 981189 reaction equation
Cl[C:2]1[C:11](C(C(=CN(C)C)C(OCC)=O)=O)=[CH:10][C:9]2[C:4](=[CH:5][C:6](Cl)=[C:7](F)[CH:8]=2)[N:3]=1.C1([NH2:29])CC1>ClC(Cl)Cl>[CH2:10]1[CH2:11][CH2:2][N:3]2[C:7](=[N:29][CH2:6][CH2:5][CH2:4]2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 54015905Ethyl 2-(2,7-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

Product 1

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneYield 122.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 20.6 g of ethyl 2-(2,7-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate and 6 g of cyclopropylamine in 100 cm3 of trichloromethane is stirred at a temperature close to 20° C. for 24 hours. The reaction mixture is concentrated under reduced pressure (20 kPa) at 50° C. The residue is taken up in 180 cm3 of ethanol and 10 g of DBU and the solution obtained is heated at a temperature close to 78° C. for 4 hours. After cooling to a temperature close to 20° C., the precipitate obtained is drained and washed with twice 60 cm3 of ethanol. 13.65 g of 8-chloro-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a pale yellow solid melting at 256° C., which is used for the subsequent steps without further purification.

Workup

  1. customclose to 20° C. for 24 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at 50° C

Sources & evidence

ORD record
ord-e4ec64c46d964d699cbb083efb2c5d24
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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