Water → HCID 10738003, compound

HRID 1069619Notes

Reaction equation

HRID 1069619 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C:7]=1[CH2:25][CH3:26])C.[NH2:28][NH2:29].O>C(O)C>[Cl:24][C:20]1[CH:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[C:6]([CH2:5][C:4]([NH:28][NH2:29])=[O:3])=[C:7]2[CH2:25][CH3:26])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 70240212HCID 70240212, compound

Product 1

HCID 10738003HCID 10738003, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.93 g (5 mmol) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetic acid ethyl ester and 5 mL of hydrazine in 20 mL of ethanol was heated to maintain reflux for 19 hours. After cooling, water was added and the mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4), and concentrated to give 1.144 g (62% yield) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetic acid hydrazide.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 19 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d09eae987a2141019a0729a03000b0ad
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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