Hydrazine → HCID 10615906, compound

HRID 1069585Notes

Reaction equation

HRID 1069585 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[CH3:24])C.[NH2:26][NH2:27]>CCO.O>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:6]([CH2:5][C:4]([NH:26][NH2:27])=[O:3])=[C:7]([CH3:24])[N:8]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 10616925HCID 10616925, compound

Product 1

HCID 10615906HCID 10615906, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Methoxy-2-methyl-l(phenylmethyl)-1H-indole-3-acetic acid hydrazide. A solution of 2.8 g (8.3 mmol) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester and 10 mL of hydrazine in 40 mL of EtOH was heated to maintain reflux for 16 hours, diluted with water and extracted with EtOAc. The EtOAc solution was washed with NaCl solution, dried (MgSO4), and concentrated at reduced pressure. The residue was crystallized from MeOH to give 2.0 g (75% yield) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide, mp, 145-147° C.

Workup

  1. temperatureto maintain
  2. temperaturereflux for 16 hours
  3. extractionextracted with EtOAc
  4. washThe EtOAc solution was washed with NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-5e71730633e74e73ac8a6288e58d70ef
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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