Water → HCID 58068469, compound

HRID 574036Notes

Reaction equation

HRID 574036 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=O.CN(C)C=O.C(Cl)(Cl)Cl.O>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:10]3[CH:11]=[CH:12][C:13]4[C:18]([C:9]3=[N:8][N:7]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 6228DimethylformamideHCID 58068864HCID 58068864, compound

Product 1

HCID 58068469HCID 58068469, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a 500-mL three-neck flask were added 6.2 g (18 mmol) of N′-(3-bromobenzoyl)-N-(1-isoquinolyl)hydrazine and 200 mL of N,N-dimethylformamide (DMF). This mixture was stirred at 120° C. for 9 hours under a nitrogen stream. After a predetermined time elapsed, this mixture was cooled to room temperature, and chloroform and water were added thereto. Organic substances were extracted from the aqueous layer with chloroform. The obtained extract solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine, and the organic layer was dried over magnesium sulfate. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1) to give a solid. A methanol suspension of this solid was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that the substance which was the object of the synthesis was obtained as 5.5 g of a white powder in 92% yield.

Workup

  1. temperaturethis mixture was cooled to room temperature
  2. extractionOrganic substances were extracted from the aqueous layer with chloroform
  3. extractionThe obtained extract solution
  4. washwas washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationThe obtained mixture was gravity-filtered
  7. concentrationthe filtrate was concentrated
  8. customto give a solid
  9. customThe obtained solid was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1)
  10. customto give a solid
  11. customwas irradiated with ultrasonic waves
  12. filtrationa solid was collected by suction filtration, so that the substance which

Sources & evidence

ORD record
ord-1f00c33ee5de4ff8b2a290dbab87c36d
Source dataset
uspto-grants-2015_05
Patent number
US09034486B2

Reaction notes

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