Dimethylamine → 1-(2-Dimethylaminoacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 589311Notes

Reaction equation

HRID 589311 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:18][NH:19][CH3:20]>C1COCC1>[CH3:18][N:19]([CH3:20])[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 125783601-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 569786941-(2-Dimethylaminoacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-chloro-1-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone (1 g, 3.9 mmol) was dissolved in 10 ml of dry THF and 7.8 ml of a 1M solution of dimethylamine in THF (7.8 mmol) were added. This reaction mixture was stirred at ambient temperature for 24 h. The solvent was removed under reduced pressure and the residue was crystallized from diethyl ether to give the expected compound 2-(dimethylamino)-1-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone in the form of a brown solid (Mp 130-132° C.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f1382a3da34e4d9f816fb1f162021e0e
Source dataset
uspto-grants-2016_01
Patent number
US09233060B2

Reaction notes

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