Pyridine → HCID 178483461, compound

HRID 1807343Notes

Reaction equation

HRID 1807343 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:15]#[C:16][Br:17]>C(OCC)C>[Br-:17].[CH3:1]/[N+:2](=[CH:10]\[CH:11]=[CH:12]\[CH:13]=[CH:14]\[N:15]([CH3:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7515N-MethylanilineHCID 10476Cyanogen Bromide

Product 1

HCID 178483461HCID 178483461, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of N-methylaniline (30 g, 140 mmol) and pyridine (11.2 g, 140 mmol) in diethylether (100 ml) at 0° C., was added a solution of cyanogen bromide (14.8 g, 140 mmol) in ether (40 ml) dropwise. The mixture was warmed to 20° C. and within 15 minutes a red oil began to separate. Exothermic (30° C.) crystallization ensued and the red solid mass was left to stand at room temperature overnight. The crystalline mass was filtered and washed with cold ether under N2 and the hygroscopic salt was used in the next step without further purification. Yield: 47.7 g (95%).

Workup

  1. customto separate
  2. customExothermic (30° C.) crystallization
  3. waitthe red solid mass was left
  4. filtrationThe crystalline mass was filtered
  5. washwashed with cold ether under N2
  6. customthe hygroscopic salt was used in the next step without further purification

Sources & evidence

ORD record
ord-7b66022784ca4157acc170d976504bfe
Source dataset
uspto-grants-2013_01
Patent number
US08357350B2

Reaction notes

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