p-Toluidine → HCID 66838477, compound

HRID 446196Notes

Reaction equation

HRID 446196 reaction equation
[P:1]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]#[N:21])[CH:14]=[CH:13]2)([O:6]CC)([O:3]CC)=[O:2].I[Si](C)(C)C.NC1C=CC(C)=CC=1>C(Cl)Cl>[C:20]([C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([O:9][P:1](=[O:2])([OH:3])[OH:6])[CH:11]=2)[N:16]=1)#[N:21]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 85247Trimethylsilyl iodideHCID 58797783Diethyl (2-cyano-quinolin-6-yl) phosphate

Product 1

HCID 66838477HCID 66838477, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of diethyl (2-cyano-quinolin-6-yl) phosphate (0.58 g, 1.86 mmol) in 10 ml of methylene chloride was added iodotrimethylsilane (0.82 g, 4.1 mmol). The resultant mixture was stirred for 40 minutes and then added to the solution of p-toluidine (1.50 g, 14.0 mmol) in 20 ml. After the solvent was partially removed, the white yellow precipitate was collected by filtration and washed with ethanol and ether to give a yield of 92%.

Workup

  1. customAfter the solvent was partially removed
  2. filtrationthe white yellow precipitate was collected by filtration
  3. washwashed with ethanol and ether
  4. customto give a yield of 92%

Sources & evidence

ORD record
ord-0157ed6fc563403a8d0ac485fce1451b
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Reaction notes

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