N-Iodosuccinimide → HCID 59696499, compound

HRID 2075286Notes

Reaction equation

HRID 2075286 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[C:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:11]=[N:12]2)=[CH:7][N:6]=1)=[O:4].[I:24]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH:11]=[N:12]2)=[C:7]([I:24])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 10335671HCID 10335671, compound

Product 1

HCID 59696499HCID 59696499, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dimethylformamide solution (200 ml) of the above Compound 6 (3.56 g, 11.4 mmol) was added N-iodo succinimide (3.06 g, 13.6 mmol), and the solution was stirred overnight at room temperature. The reaction solution was distilled off under reduced pressure, and the residue was added with chloroform, washed with 10% sodium hydrogen sulfite aqueous solution and water, and dried over anhydrous sodium sulfate, and then the solvent was distilled off. Precipitated crystals were collected by filtering, and washed with methanol to give 3-(4-fluorobenzyl)-8-hydroxy-5-iodo[1,6]naphthyridine-7-carboxylic acid methyl ester 7 (4.97 g) in 99% yield.

Workup

  1. distillationThe reaction solution was distilled off under reduced pressure
  2. additionthe residue was added with chloroform
  3. washwashed with 10% sodium hydrogen sulfite aqueous solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customPrecipitated crystals
  7. customwere collected
  8. filtrationby filtering
  9. washwashed with methanol

Sources & evidence

ORD record
ord-60672455fe7d4195b5d3a726a3f7a4fd
Source dataset
uspto-grants-2011_04
Patent number
US07919623B2

Reaction notes

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