Oxalyl chloride → Indole-3-acetamide

HRID 2292807Notes

Reaction equation

HRID 2292807 reaction equation
C([C:3]1[N:4](CC2C=CC=CC=2)[C:5]2[C:10]([C:11]=1[C:12](=O)[C:13]([NH2:15])=[O:14])=[C:9](OC)[CH:8]=[CH:7][CH:6]=2)C.C(Cl)(=O)C(Cl)=O.C(C1N(CC2C=CC=CC=2)C2C(C=1)=C(OC)C=CC=2)C>C(Cl)Cl>[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([CH2:12][C:13]([NH2:15])=[O:14])=[CH:3]1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 99432411-Benzyl-2-ethyl-4-methoxy-1H-indoleHCID 10830680HCID 10830680, compound

Product 1

HCID 397Indole-3-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Ethyl-4-methoxy-alpha-oxo-1-(phenylmethyl)-1H-indole-3-acetamide. Oxalyl chloride (0.87 mL, 10 mmol) was added to 2.6 g (9.8 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole in 25 mL of methylene chloride, the mixture stirred for 3 hours and concentrated at reduced pressure. The residue was redissolved in 25 mL of methylene chloride, anhydrous ammonia bubbled in for 0.25 hours and the mixture concentrated. The residue was stirred with ethyl acetate/water and the insoluble material filtered. The ethyl acetate from the filtrate was washed with brine, dried (MgSO4) and concentrated. The residue was washed with ether and combined with the filtered material above to give 1.19 g (36% yield) of 2-ethyl-4-methoxy-alpha-oxo-1-phenylmethyl)-1H-indole-3-acetamide, mp, 193°-199° C.

Workup

  1. concentrationconcentrated at reduced pressure
  2. dissolutionThe residue was redissolved in 25 mL of methylene chloride
  3. customanhydrous ammonia bubbled in for 0.25 hours
  4. concentrationthe mixture concentrated
  5. stirringThe residue was stirred with ethyl acetate/water
  6. filtrationthe insoluble material filtered
  7. washThe ethyl acetate from the filtrate was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. washThe residue was washed with ether

Sources & evidence

ORD record
ord-b258401395af4bd2af16dddc53c231ba
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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