3-Bromophenylhydrazine hydrochloride → HCID 10286296, compound

HRID 2099513Notes

Reaction equation

HRID 2099513 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]([CH:10]=O)[CH:8]=O)[N:4]=[CH:3][CH:2]=1.Cl.[Br:13][C:14]1[CH:15]=[C:16]([NH:20][NH2:21])[CH:17]=[CH:18][CH:19]=1>C(O)C>[Br:13][C:14]1[CH:15]=[C:16]([N:20]2[CH:10]=[C:7]([C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=3)[CH:8]=[N:21]2)[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 27372452-(2-Pyridyl)malondialdehyde

Product 1

HCID 10286296HCID 10286296, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-(2-Pyridyl)malondialdehyde (100 mg, 0.67 mmol) and 3-bromophenylhydrazine hydrochloride (150 mg, 0.67 mmol) were suspended in ethanol (2 mL), and heated to 75° C. for 8 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel preparative TLC eluting with hexanes:EtOAc (3:1) to afford 2-[1-(3-bromophenyl)-1H-pyrazol-4-yl]pyridine as a pale yellow solid. 1H-NMR (CDCl3, 300 MHz) δ 8.61 (d, J=4.8 Hz, 1H), 8.51 (s, 1H), 8.18 (s, 1H), 7.99 (s, 1H), 7.73-7.68 (m, 2H), 7.55 (d, J=7.9 Hz, 1H), 7.43 (d, J=8.8 Hz, 1H), 7.35 (t, J=8.1 Hz, 1H), 7.17 (dd, J=4.9, 7.4 Hz, 1H). MS (ESI) 300.0, 302.0 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel preparative TLC
  3. washeluting with hexanes:EtOAc (3:1)

Sources & evidence

ORD record
ord-93dc8dbeffec4bee8573a18d5e4535d9
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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