Phenylhydrazine → HCID 71295572, compound

HRID 1776834Notes

Reaction equation

HRID 1776834 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[C:13]1([NH:19]N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8]2[NH:19][C:13]3[C:18]([CH:9]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:7]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 27570291-(5-bromo-2-methoxyphenyl)ethanone

Product 1

HCID 71295572HCID 71295572, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 1-(5-bromo-2-methoxyphenyl)ethanone (10 g, 43.6 mmol), phenylhydrazine (7.07 g, 65.5 mmol) was stirred in PPA (50 mL) at 110° C. for 2 hours. The reaction mixture was added to water and basified to pH=7, then extracted with ethyl acetate and washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using column chromatography to provide the product of 2-(5-bromo-2-methoxyphenyl)-1H-indole (10 g, yield: 71%). 1H-NMR (CDCl3, 400 MHz) δ 9.57 (s, 1H), 7.93 (d, J=2.4 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.34˜7.42 (m, 2H), 7.09˜7.21 (m, 2H), 6.90 (d, J=8.8 Hz, 1H), 4.00 (s, 3H). MS (M+H)+: 302/304.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-f68f82b705ee4f0f80cf1dae345c3ba3
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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