Ethanol → HCID 20186934, compound

HRID 2420527Notes

Reaction equation

HRID 2420527 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[CH:2]1.[C-]#[N:13].[K+].[CH2:15]([OH:17])C.O.C[N:20]([CH:22]=[O:23])C>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[NH:13][C:22](=[O:23])[NH:20][C:15]2=[O:17])=[CH:2]1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 10256Indole-3-Carboxaldehyde

Product 1

HCID 20186934HCID 20186934, compound

Procedure

A mixture of indole-3-carboxaldehyde (43.6 g, 0.3 mole), KCN (29.3 g, 0.45 mole), (NH4)2CO3 (144 g, 1.5 mole), 250 ml of C2H5OH, 250 ml of H2O and 200 ml of DMF was warmed with stirring at 70°-80° for 16 hours. The dark solution was filtered, cooled and acidified with concentrated HCl. The solid was collected, dissolved in dilute NaOH, filtered and acidified with dilute HCl. The solid was collected and recrystallized from aqueous methanol, yield 28.5 g, mp 229°-30°.

Workup

  1. temperaturewas warmed
  2. filtrationThe dark solution was filtered
  3. temperaturecooled
  4. customThe solid was collected
  5. dissolutiondissolved in dilute NaOH
  6. filtrationfiltered
  7. customThe solid was collected
  8. customrecrystallized from aqueous methanol, yield 28.5 g, mp 229°-30°

Sources & evidence

ORD record
ord-7c5917cda77142698416be1fa4fc93f2
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

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