Indole-5-carboxaldehyde → HCID 86598195, compound

HRID 2223199Notes

Reaction equation

HRID 2223199 reaction equation
C[O-].[Na+].[Na].[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]=O)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[N:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[N+:17]=[N-:18]>O.CO>[N:16](/[C:19](=[CH:14]\[C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][CH:6]=[CH:7]2)/[C:20]([O:22][CH3:23])=[O:21])=[N+:17]=[N-:18]

Participants

7

Reactant 4

HCID 589040Indole-5-carboxaldehydeHCID 4020482Methyl 2-azidoacetateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 86598195HCID 86598195, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Under nitrogen, to a sodium methoxide solution (prepared from 15 ml of methanol and 0.66 g (29 mmol) of sodium) a mixture of 1.02 g (7 mmol) of indole-5-carbaldehyde [Helv. Chim. Acta, 1616. (1968)], 3.34 g (29 mmol) of methyl azido-acetate and 7 ml of methanol is added dropwise at 0° C. and the so obtained mixture is stirred at this temperature for 5 h. Then the reaction mixture is diluted with 50 ml of water, and extracted three times with: 50 ml of chloroform. The combined organic layers are washed with 20 ml of water, filtered through a phase separating filter-paper and concentrated to yield 1.3 g (77%) of the title compound. Mp.: 130-133° C. (chloroform).

Workup

  1. additionis added dropwise at 0° C.
  2. extractionextracted three times with: 50 ml of chloroform
  3. washThe combined organic layers are washed with 20 ml of water
  4. filtrationfiltered through a phase
  5. customseparating
  6. filtrationfilter-paper
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bc5e51d5d75a4733b64bf47dc48262fb
Source dataset
uspto-grants-2008_05
Patent number
US07375116B2

Reaction notes

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