Nitric Acid → N,N-Dimethyl-2-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine

HRID 1922406Notes

Reaction equation

HRID 1922406 reaction equation
[N:1]1([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.OS(O)(=O)=O.[N+:21]([O-])([OH:23])=[O:22].[OH-].[Na+]>O>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:21]([O-:23])=[O:22])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 2305312-(3,4-Dihydroquinolin-1(2h)-yl)-n,n-dimethylethanamine

Product 1

HCID 58874105N,N-Dimethyl-2-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of compound 3 (0.87 g, 4.285 mmol) in con. H2SO4 (10 mL) was treated with fuming HNO3 (0.2 mL, 4.285 mmol, 90%) drop wise over a period of 10 min. at 0° C. and was stirred at same temperature for additional 20 min. The reaction was diluted with water (50 mL), basified to pH ˜10 using 2 N NaOH solution and product was extracted into CH2Cl2 (3×20 mL). The combined organic layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5 to obtain compound 4 (0.85 g, 80%) including some dinitro derivative, which was separated at later stage.

Workup

  1. extractionwas extracted into CH2Cl2 (3×20 mL)
  2. washThe combined organic layer was washed with brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH

Sources & evidence

ORD record
ord-f762822f563c4cdaa4f253391ad9239f
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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