Water → HCID 14256066, compound

HRID 1995415Notes

Reaction equation

HRID 1995415 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH:10]([OH:17])[CH2:11][NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[C:4]([C:5]#[N:6])[C:3]=1[NH2:18].CCCCC.[OH2:24]>[OH-].[Na+].CCO>[NH2:18][C:3]1[C:2]([Br:1])=[CH:9][C:8]([CH:10]([OH:17])[CH2:11][NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:7][C:4]=1[C:5]([NH2:6])=[O:24]

Participants

6

Reactant 3

HCID 962WaterHCID 8003PentaneHCID 42003HCID 42003, compound

Product 1

HCID 14256066HCID 14256066, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture containing 1.02 g of 3-bromo-5-[2-(tert-butylamino)-1-hydroxyethyl]anthranilonitrile in 25 ml of H2O, 5 ml of 50% NaOH and 30 ml of EtOH is stirred and heated at 55°-65° C. under N2 atmosphere for 1.25 hours. The mixture is evaporated to remove EtOH and extracted with CHCl3. The CHCl3 extract is washed with 25 ml of 2% NaOH, dried (MgSO4) and evaporated to dryness to afford 0.74 g. This solid is stirred with pentane and filtered to afford 0.6 g, mp 135°-145° C., of the title compound.

Workup

  1. temperatureheated at 55°-65° C. under N2 atmosphere for 1.25 hours
  2. customThe mixture is evaporated
  3. customto remove EtOH
  4. extractionextracted with CHCl3
  5. extractionThe CHCl3 extract
  6. washis washed with 25 ml of 2% NaOH
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customto afford 0.74 g
  10. filtrationfiltered
  11. customto afford 0.6 g, mp 135°-145° C.

Sources & evidence

ORD record
ord-16e516d2790940389e97c21045600f8e
Source dataset
uspto-grants-1983_09
Patent number
US04404222

Reaction notes

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