Water → HCID 10785116, compound

HRID 2292803Notes

Reaction equation

HRID 2292803 reaction equation
CO[C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:23][C:24]([NH2:26])=[O:25])=[C:9]([CH3:22])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:28][NH2:29].C(OCC)(=O)C.O>C(O)C>[NH:28]([C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:23][C:24]([NH2:26])=[O:25])=[C:9]([CH3:22])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 10761402HCID 10761402, compound

Product 1

HCID 10785116HCID 10785116, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 484 mg (1.3 mmol) of 2-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester (Example 39) and 2 mL of hydrazine in 10 mL of ethanol was heated to maintain reflux for 16 hours, 10 mL of ethanol added, heated an additional 4 hours and cooled. Ethyl acetate and water were added and the insoluble material filtered. The ethyl acetate solution was separated, washed with brine, dried (MgSO4) and concentrated. The residue was combined with the precipitate above to give 435 mg (91% yield) of 4-(2-hydrazino-2-oxoethoxy)-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 207°-210° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 16 hours
  4. temperatureheated an additional 4 hours
  5. temperaturecooled
  6. filtrationthe insoluble material filtered
  7. customThe ethyl acetate solution was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bc5cf67191904dc0aea9051d4ab78114
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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