Potassium Hydroxide → HCID 20238660, compound

HRID 364964Notes

Reaction equation

HRID 364964 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1O[N:7]=[CH:8][C:9]1[NH:10][C:11]([CH2:34][F:35])=[C:12]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])([O-])=O.[OH-].[K+]>C(O)C>[C:8]([C:9]1[NH:10][C:11]([CH2:34][F:35])=[C:12]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 73666402HCID 73666402, compound

Product 1

HCID 20238660HCID 20238660, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of step (a) (0.45 g, 0.8 mmoles) was dissolved in 95% aqueous ethanol (20 ml) by heating, and then potassium hydroxide (10.16 ml of 0.2M in 95% aqueous ethanol) was added dropwise. The solution was heated at reflux for 3 hours and then the ethanol removed in vacuo. The residue was dissolved in water (75 ml), 5% aqueous sodium hydroxide (6 ml) and chloroform (100 ml). The aqueous layer was separated and extracted several times with chloroform. The combined extracts were washed with water, dried (MgSO4) and the solvent was removed in vacuo. The residue was crystallised from 2-propanol to give the title compound (0.19 g) mp 147°-8° (dec.).

Workup

  1. temperatureby heating
  2. temperatureThe solution was heated
  3. temperatureat reflux for 3 hours
  4. customthe ethanol removed in vacuo
  5. dissolutionThe residue was dissolved in water (75 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted several times with chloroform
  8. washThe combined extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. customthe solvent was removed in vacuo
  11. customThe residue was crystallised from 2-propanol

Sources & evidence

ORD record
ord-8aabcfbdf9b94bdda0c327ddaaabd01d
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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