Sodium Carbonate → 6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine

HRID 327461Notes

Reaction equation

HRID 327461 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[NH:10][CH2:9][CH:8]([NH2:17])[CH2:7]2.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[NH:10][CH2:9][CH:8]([N:17]([CH2:7][CH2:6][CH3:11])[CH2:13][CH2:4][CH3:5])[CH2:7]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 199193576-Bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride

Product 1

HCID 199194006-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamineYield 139.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride (11.5 g, 0.033 mol), idopropane (21 g, 0.12 mol) and anhydrous sodium carbonate (20 g, 0.19 mol) in dimethylformamide (100 mL) was stirred at 100° C. for 5 hours. The solution was then evaporated, partitioned between ethyl acetate and water, and the ethyl acetate was evaporated to give a red oil. This was chromatographed on silica gel to give 8.2 g of 6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine. The product was crystallized from ethyl acetate:hexane to give 7.6 g of product, mp 79°-81° C. Anal. Calcd. for C15H22BrN3O2 : C, 50.57; H, 6.23; Br, 22.43; N, 11.79. Found: C, 50.59; H, 6.27; Br, 22.53; N, 11.69.

Workup

  1. customThe solution was then evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe ethyl acetate was evaporated
  4. customto give a red oil
  5. customThis was chromatographed on silica gel

Sources & evidence

ORD record
ord-bddad193d4514285ad1f9dd0b3360219
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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