Phenylhydrazine → HCID 271464, compound

HRID 1593624Notes

Reaction equation

HRID 1593624 reaction equation
N1C2C(=CC=CC=2)C=C1C(N)=O.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[C:21]1([NH:27][NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.NN>O.C(O)C>[C:21]1([NH:27][N:28]=[C:18]2[C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7516Phenylhydrazine2×HCID 9321HydrazineHCID 104341,3-CyclohexanedioneHCID 5948321H-Indole-2-carboxamide

Product 1

HCID 271464HCID 271464, compoundYield 83,386.797%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

The title compound was prepared by a modification of published procedures (M. S. Berridge et al., Nucl. Med. Biol. 19 (5) 563-569 (1992); Brueckner R. et al., EP 1 424 337 A1 (2004)). To a stirred suspension of cyclohexane-1,3-dione (10 g, 0.089 mol) in water (64 mL) under nitrogen was added via dropping funnel 10-15 drops of a solution of phenylhydrazine (8.8 mL, 0.089 mmol) in water (124 mL). The mixture was stirred for 15 minutes at room temperature and then the remainder of the phenylhydrazine solution was added dropwise over a 4 hour period. Ethanol (21 mL) was added to facilitate stirring after about 30 mL of the hydrazine solution had been added. Stirring was continued for an additional 30 minutes. The orange solid was collected by filtration, washed with water and a small amount of 3:1 (v/v) water-ethanol, and dried in vacuo overnight to provide the title compound (15.01 g, 83.3%). MS (ES): [M+H]+ @m/z 203.1

Workup

  1. additionwas added
  2. additionhad been added
  3. stirringStirring
  4. waitwas continued for an additional 30 minutes
  5. filtrationThe orange solid was collected by filtration
  6. washwashed with water
  7. dry with materiala small amount of 3:1 (v/v) water-ethanol, and dried in vacuo overnight

Sources & evidence

ORD record
ord-80733db373de48e6adce0da5dfdc5b51
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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