4-Chloroquinoline → HCID 22935746, compound

HRID 1352493Notes

Reaction equation

HRID 1352493 reaction equation
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=O)[CH2:11][CH:10]1[CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([N:29]1C2C(=CC(Cl)=CC=2)C(=O)CC1C)(=O)[C:22]1C=CC=C[CH:23]=1.ClC1C2C(=CC=CC=2)N=CC=1.C(N)C#C>ClC(Cl)C.C1(C)C=CC=CC=1.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].C(N(CC)CC)C>[CH3:20][CH:10]1[CH2:11][C:12](=[N:29][CH2:21][C:22]#[CH:23])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

9

Reactant 4

HCID 691404-ChloroquinolineHCID 239041PropargylamineHCID 22935722HCID 22935722, compoundHCID 229357231-Benzoyl-2-methyl-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 22935746HCID 22935746, compound

Reagents, catalysts & solvents 4

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 1140TolueneSolventHCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 1-benzoyl-2-methyl-2,3-dihydro-1H-quinolin-4-one (corresponds to a compound of general formula (3b) wherein R3 is phenyl, R4 is CH3 and R5, R6, R7, R8 are H, prepared as disclosed in example 46, according to protocol B, starting from 4-chloro-quinoline, (0.3 g), triethylamine (0.92 g), propargyl amine (0.125 g) in dichloroethane (20 ml), cooled at −5° C. in an ice/sodium chloride bath, a solution of titanium chloride in toluene 1 mol/l was dropwise added for 10 minutes. The mixture was stirred over night at room temperature and then washed with dichloromethane and an aqueous solution of potassium carbonate. The organic layer was separated, dried over sodium sulfate and the solvent was removed under reduced pressure to give (2-methyl-4-prop-2-ynylimino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (brown oil) (0.5 g) which was not purified, but directly used in the next step

Workup

  1. customprepared
  2. washwashed with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-220a9c2554d34ab69b90083204b7b1ff
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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