Sodium Azide → (8-Methyl-2-o-tolylquinolin-3-yl)methanamine

HRID 1397657Notes

Reaction equation

HRID 1397657 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:13].[N-:21]=[N+]=[N-].[Na+]>CS(C)=O>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[C:3]([CH2:2][NH2:21])=[CH:12]2

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 575561733-(Chloromethyl)-8-methyl-2-o-tolylquinoline

Product 1

HCID 57707793(8-Methyl-2-o-tolylquinolin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared according to Procedure D using 3-(chloromethyl)-8-methyl-2-o-tolyl-quinoline (667 mg, 2.4 mmol) in DMSO (10 mL) was added NaN3 (500 mg, 3 eq). After purification, (8-methyl-2-o-tolylquinolin-3-yl)methanamine was obtained as pale yellow oil.

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-848d113c0f4a4910b2eb8396c804fe6a
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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