N,N-Dimethylethylenediamine → HCID 178483763, compound

HRID 513693Notes

Reaction equation

HRID 513693 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[C:25]([N+:26]([O-])=O)=[C:24]3[C:19]([CH:20]=[CH:21][CH:22]=[N:23]3)=[CH:18][CH:17]=2)=O)=[CH:10][CH:9]=1.CCOC(C)=O.[Cl-].[Na+].O>C(Cl)Cl.C1COCC1>[NH2:26][C:25]1[C:16](/[C:14](=[N:5]/[CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])/[C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=2)=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 68183178HCID 68183178, compoundHCID 131718255Brine ethyl acetate

Product 1

HCID 178483763HCID 178483763, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

N,N dimethylethylenediamine (2.5 ml, 3.37 mmol) and Ti(OEt)4 (1.16 ml, 5.46 mmol) were added to a solution of (4-fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanone 352 (400 mg, 1.35 mmol) in DCM/THF(10 ml:40 ml) under an argon atmosphere and the mixture was stirred at room temperature for 18 h. The mixture was poured into EtOAc/brine and the resulting solution was filtered through celite. The solid residue was washed with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (414 mg, 91%) which was used in the next step without further purification.

Workup

  1. filtrationthe resulting solution was filtered through celite
  2. washThe solid residue was washed with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d278a2b81091431381d08b3db252795c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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