Indole-5-carboxaldehyde → HCID 86598195, compound

HRID 896411Notes

Reaction equation

HRID 896411 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-eeb1b046ea4740ef858dd95dcd1345f1
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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