Glyceraldehyde → HCID 70126668, compound

HRID 1376790Notes

Reaction equation

HRID 1376790 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.[Cl-].C[NH3+].C([BH3-])#N.[Na+].[O:29]=[CH:30][CH:31]([CH2:33]O)[OH:32].C#N>CO>[OH:32][CH:31]([CH2:30][OH:29])[CH2:33][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1

Participants

7

Reactant 5

HCID 751GlyceraldehydeHCID 768Hydrogen CyanideHCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 53909416HCID 53909416, compound

Product 1

HCID 70126668HCID 70126668, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-amino-3-[(7-azaindol-3-yl) methylen]-2-oxindole (2.773 g, 10 mmol) in methanol (30 ml) was added anhydrous methylammonium chloride (0.60 g, 10 mmol). Then sodium cyanoborohydride (0.378 g, 6 mmol) was added in portions. Finally, glyceraldehyde (0.901 g, 10 mmol) was added portionwise over 30 min and the solution stirred at room temperature for 50 h. Ice cold 6N HCl was added until gas evolution (HCN) stopped and the pH of the solution was 2. The methanol was evaporated in vacuo and the remaining aqueous solution was washed with CHCl3. Solid KOH was added until the pH was 12. Solid NaCl was added to saturation and the solution extracted twice with CHCl3. The CHCl3 extracts were washed with saturated NaCl solution, dried over K2CO3 and evaporated. The residue was chromatographed on silica gel using CHCl3 --MeOH mixtures as eluant. Thus pure title compound was obtained in about 60% yield.

Workup

  1. customThe methanol was evaporated in vacuo
  2. washthe remaining aqueous solution was washed with CHCl3
  3. additionSolid KOH was added until the pH was 12
  4. additionSolid NaCl was added to saturation
  5. extractionthe solution extracted twice with CHCl3
  6. washThe CHCl3 extracts were washed with saturated NaCl solution
  7. dry with materialdried over K2CO3
  8. customevaporated
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-6962a0aba935495784997b4a41d51cb0
Source dataset
uspto-grants-1997_09
Patent number
US05663346

Reaction notes

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