Allyl bromide → HCID 57698807, compound

HRID 552376Notes

Reaction equation

HRID 552376 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[C:5](ON=O)(C)(C)C.CN[C:14]1[C:15](=[C:19]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:21][CH:22]=1)[C:16]([OH:18])=[O:17]>C(#N)C>[CH2:1]([C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:15]=1[C:16]([O:18][CH3:5])=[O:17])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10906Tert-Butyl nitriteHCID 45089399HCID 45089399, compound

Product 1

HCID 57698807HCID 57698807, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of allyl bromide (39.7 ml, 459.18 mmol) and tert-butylnitrite (5.5 ml, 45.91 mmol) in acetonitrile (30 ml) was added methyl 6-nitroanthranilic acid (6.0 g, 30.61 mmol) portion-wise at room temperature and the mixture was further stirred for 1 h. The volatile components were evaporated under reduced pressure and the residue was diluted with water. The mixture was extracted with ethyl acetate (2×50 ml) and the combined organic extracts were washed with water and dried over anhydrous sodium sulfate. The residue obtained after evaporation of the solvent was purified by silica gel column chromatography using 5% ethyl acetate in petroleum ether as eluent to give 4.2 g of the product as a yellow oil; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.99 (d, J=7.8, 1H); 7.58-7.46 (m, 2H); 5.93-5.80 (m, 1H), 5.15-5.03 (m, 2H); 3.93 (s, 3H); 3.46 (d, J=6.0, 2H).

Workup

  1. customThe volatile components were evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. customafter evaporation of the solvent
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6ceec7506324cc3ac0fc4b013b66174
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Reaction notes

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