Indole-3-Carboxaldehyde → HCID 54364322, compound

HRID 1973553Notes

Reaction equation

HRID 1973553 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1.[CH3:14][C:15]1([CH2:20][CH2:21][CH2:22]Cl)[O:19][CH2:18][CH2:17][O:16]1>CN(C)C=O>[CH3:14][C:15]1([CH2:20][CH2:21][CH2:22][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH:12]=[O:13])=[CH:4]2)[O:19][CH2:18][CH2:17][O:16]1

Participants

5

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolane

Product 1

HCID 54364322HCID 54364322, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 10.6 g. (0.44 mole) of sodium hydride in 50 ml. of dry dimethylformamide is treated dropwise with a solution of 58 g. (0.40 mole) of indole-3-carboxaldehyde in 200 ml. of dimethylformamide. An exothermic reaction is observed with the temperature rising to 70° C. The resulting mixture is stirred for one hour. To the resulting mixture there is added 69 g. (0.42 mole) of 2-methyl-2(3-chloropropyl)-dioxolane, and the mixture is maintained overnight at room temperature. The solvent is evaporated and the residue is extracted with ether, washed with water and dried over anhydrous magnesium sulfate. Following the evaporation of the solvent, the residue is crystallized from ether/hexane to give 1-[3-(2-methyl-2-dioxolanyl)propyl]-3-indolecarboxaldehyde, m.p. 52°-55° C.

Workup

  1. additionA suspension of 10.6 g
  2. customAn exothermic reaction
  3. customrising to 70° C
  4. additionTo the resulting mixture there is added 69 g
  5. customThe solvent is evaporated
  6. extractionthe residue is extracted with ether
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe evaporation of the solvent
  10. customthe residue is crystallized from ether/hexane

Sources & evidence

ORD record
ord-1854997f7cf04b69b02501796188a3f0
Source dataset
uspto-grants-1976_12
Patent number
US03997670

Reaction notes

Loading…