Water → HCID 58345598, compound

HRID 2381248Notes

Reaction equation

HRID 2381248 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[C:4]([C:6]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([OH:17])[C:11]([OH:18])=[CH:10][C:7]=1[C:8]#[N:9])=[O:5].[C:23](Cl)(=[O:27])[O:24][CH2:25][CH3:26].CN(C)C=O.O>C(OCC)(=O)C>[CH2:25]([O:24][C:23]([O:18][C:11]1[C:12]([OH:17])=[C:13]([N+:14]([O-:16])=[O:15])[C:6]([C:4](=[O:5])[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=2[F:1])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 58345633HCID 58345633, compound2×

Product 1

HCID 58345598HCID 58345598, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2-fluorobenzoyl)-4,5-dihydroxy-3-nitrobenzonitrile (compound 1-29) (70 mg), ethyl chloro-carbonate (30 mg) and N,N-dimethylforamide (1 mL) was stirred at 50° C. for 3 hours. Water and ethyl acetate were added to the mixture. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 50-100% ethyl acetate/hexane, gradient elution) to give the title compound (60 mg). The structural formula was illustrated in table 10.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: 50-100% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-e07f61f123df4ea381edcbebf563e04f
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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