Hydrazine hydrate (1:1) → HCID 136359794, compound

HRID 2361374Notes

Reaction equation

HRID 2361374 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:19](=O)[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:21]=3[CH3:29])=[C:11]([C:15]([O:17]C)=O)[NH:12]2)=[CH:8][CH:7]=1.O.[NH2:32][NH2:33]>C(O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:21]=4[CH3:29])=[N:33][NH:32][C:15](=[O:17])[C:11]=3[NH:12][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67994951HCID 67994951, compound

Product 1

HCID 136359794HCID 136359794, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A yellow, homogeneous solution of methyl 6-(2-methoxyethoxy)-3-(2-methyl-3-nitrobenzoyl)-1H-indole-2-carboxylate (1.546 g, 3.75 mmol) and hydrazine hydrate (0.982 mL, 13.13 mmol) in ethanol (55.1 mL) under nitrogen was refluxed overnight. The reaction was cooled to room temperature and concentrated in vacuo. It was dissolved in EtOAc (150 mL) and washed with water (40 mL) and brine (40 mL), dried over MgSO4, and concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 120 g column eluting with 0-100% EtOAc/hexanes. Appropriate fractions were collected and concentrated in vacuo to give the desired product (0.7461 g, 1.892 mmol, 50.4% yield) as a light yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionIt was dissolved in EtOAc (150 mL)
  3. washwashed with water (40 mL) and brine (40 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by flash chromatography
  8. washeluting with 0-100% EtOAc/hexanes
  9. customAppropriate fractions were collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87764a9a07cd41dc813c71ea269ece33
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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