Water → HCID 14054678, compound

HRID 1722715Notes

Reaction equation

HRID 1722715 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:12])[C:9]=1[O:10][CH3:11])[CH:5]=O.C1C(/C=N/O)=CC=[N+:17](C[N+]2C=CC(/C=N/O)=CC=2)C=1.[Br-].[Br-].B.O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:12])[C:9]=1[O:10][CH3:11])[CH2:5][NH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 14798Sodium HydroxideHCID 178492963HCID 178492963, compound

Product 1

HCID 14054678HCID 14054678, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,5-dichloro-4-methoxybenzaldehyde methoxime (10.7 g, 46 mmol) in freshly distilled tetrahydrofuran (THF) (60 ml) was cooled to 0° and stirred while 47 ml of 0.98M borane in THF was added. The resulting mixture was heated under reflux for 2 hours, cooled, and water (20 ml) added followed by 20% aqueous sodium hydroxide (20 ml). The mixture was heated under reflux for 2 hours, cooled and extracted twice with diethyl ether. The organic layer was extracted with 3N HCl, the aqueous layer made basic with 50% aqueous sodium hydroxide and the product was extracted into diethyl ether. The organic extracts were dried (Na2SO4) and concentrated to give 6.11 g (65%) of the title compound as a pale yellow oil.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for 2 hours
  7. temperaturecooled
  8. extractionextracted twice with diethyl ether
  9. extractionThe organic layer was extracted with 3N HCl
  10. extractionthe product was extracted into diethyl ether
  11. dry with materialThe organic extracts were dried (Na2SO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-440a3a526b14455b8fc22aaa5b203129
Source dataset
uspto-grants-1989_08
Patent number
US04857540

Reaction notes

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