Water → HCID 10785116, compound

HRID 1069623Notes

Reaction equation

HRID 1069623 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 he precipitate above co 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
  11. customprecipitate above co

Sources & evidence

ORD record
ord-60fba1b4b0004a37b1428b707c16fa94
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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