2,2,3-Tribromopropanal → 3-Bromo-8-iodo-6-nitro-quinoline

HRID 2421533Notes

Reaction equation

HRID 2421533 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Br:12][C:13](Br)([CH2:16]Br)[CH:14]=O>C(O)(=O)C>[Br:12][C:13]1[CH:14]=[N:4][C:3]2[C:5]([CH:16]=1)=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=2[I:1]

Participants

4

Reactant 2

HCID 931082,2,3-TribromopropanalHCID 2226292-Iodo-4-nitroaniline

Product 1

HCID 672145383-Bromo-8-iodo-6-nitro-quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

2-Iodo-4-nitroaniline (5.3 g) in acetic acid (40 ml) was treated with 2,2,3 tribromopropanal (5.9 g) and the mixture was heated at 110° C. for 2 h after which it was cooled to room temperature and filtered. The filtered solid was washed with diethyl ether, suspended in water and treated with saturated sodium hydrogen carbonate. Extraction with ethyl acetate, drying over sodium sulphate, filtration and evaporation under reduced pressure gave the desired product, 3-bromo-8-iodo-6-nitro-quinoline, as a yellow solid after chromatography (silica; hexane/ethyl acetate) (M+379).

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered
  3. washThe filtered solid was washed with diethyl ether
  4. additiontreated with saturated sodium hydrogen carbonate
  5. extractionExtraction with ethyl acetate
  6. dry with materialdrying over sodium sulphate, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-08471c38a077483687d36395e1161e86
Source dataset
uspto-grants-2011_06
Patent number
US07956188B2

Reaction notes

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