Hydrazine hydrate (1:1) → HCID 68328191, compound

HRID 634333Notes

Reaction equation

HRID 634333 reaction equation
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15]C)=O)[CH:11]=2)[NH:6][CH:5]=1)([O-:3])=[O:2].O.[NH2:18][NH2:19]>CCO>[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([NH:18][NH2:19])=[O:15])[CH:11]=2)[NH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68328398HCID 68328398, compound

Product 1

HCID 68328191HCID 68328191, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl 3-nitro-1H-indole-5-carboxylate (2.0 g, 9.09 mmol) in EtOH (40 mL) was added hydrazine hydrate (6 mL) and the reaction mixture was heated to reflux for 30 h. The mixture was cooled to RT and EtOH was removed in vacuo. Petroleum ether was added to the residue to get a yellow precipitate. The precipitate was filtered, washed with petroleum ether (3×40 mL) and dried to afford 3-nitro-1H-indole-5-carbohydrazide (1.0 g, 50%) as a yellow solid. MS (ESI, pos. ion) m/z: 221.0 (M+1); 1H NMR (300 MHz, DMSO-d6): δ 9.83 (s, 1H), 8.71 (s, 1H), 8.57 (s, 1H), 7.77 (dd, 1H, J=8.7, 1.2 Hz), 7.58 (d, 1H, J=8.7 Hz), 4.49 (brs, 2H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 30 h
  3. customEtOH was removed in vacuo
  4. additionPetroleum ether was added to the residue
  5. customto get a yellow precipitate
  6. filtrationThe precipitate was filtered
  7. washwashed with petroleum ether (3×40 mL)
  8. customdried

Sources & evidence

ORD record
ord-d8b82ca2d2b14d09a25e671f5a3e1c15
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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