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

HRID 327462Notes

Reaction equation

HRID 327462 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH:6]([NH2:15])[CH2:5]2.C=O>C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH:6]([N:15]([CH2:5][CH2:4][CH3:9])[CH2:11][CH2:2][CH3:3])[CH2:5]2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 159377596-Bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine

Product 1

HCID 199194006-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamineYield 0.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine (1.5 g, 5.5 mol), 37% aqueous formaldehyde (1.8 mL) and formic acid (10 mL) was heated at 100° C. for 1 hour. The solution was then evaporated, partitioned between ethyl acetate (200 mL) and 4 N sodium hydroxide solution (10 mL), and the ethyl acetate was evaporated to give a red oil. This was chromatographed on silica gel to give 1.58 g of 6-bromo-1,2,3,4-tetrahydro-8-nitro-N,N-dipropyl-3-quinolinamine. The product was crystallized from ethyl acetate:hexane; mp 88°-91° C. Anal. Calcd. for C11H14BrN3O2 : C, 44.01; H, 4.70; Br, 26.62; N, 14.00. Found: C, 44.04; H, 4.89; Br, 26.62; N, 13.97.

Workup

  1. customThe solution was then evaporated
  2. custompartitioned between ethyl acetate (200 mL) and 4 N sodium hydroxide solution (10 mL)
  3. customthe ethyl acetate was evaporated
  4. customto give a red oil
  5. customThis was chromatographed on silica gel

Sources & evidence

ORD record
ord-e5cd7a71a1144c408a35afb08164d314
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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