Methanol → HCID 68453627, compound

HRID 2358388Notes

Reaction equation

HRID 2358388 reaction equation
[NH2:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[I:14].CO>C1COCC1>[NH2:7][CH2:6][C:5]1[CH:8]=[C:9]([C:10]([F:12])([F:13])[F:11])[C:2]([NH2:1])=[C:3]([I:14])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 684539954-Amino-3-iodo-5-(trifluoromethyl)benzonitrile

Product 1

HCID 68453627HCID 68453627, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-3-iodo-5-trifluoromethylbenzonitrile (1805.2 mg, 5.19 mmol) was dissolved in THF at 0° C. After Borane-THF complex (3 eq, 17.36 mmol, 17.36 ml) was slowly added into the reaction mixture, A reaction temperature was heated to reflux. The reaction mixture was stirred for 12 hr with reflux. After confirming the completion of the reaction, MeOH was added. The mixture was stirred for 4 hr. The reaction solvent was removed in vacuo. A residue was extracted with Ethyl acetate, washed with H2O and brine, dried with Na2SO4 and concentrated in vacuo to yield 4-Aminomethyl-2-iodo-6-trifluoromethylphenylamine (55.1 mg).

Workup

  1. additionAfter Borane-THF complex (3 eq, 17.36 mmol, 17.36 ml) was slowly added into the reaction mixture
  2. temperatureA reaction temperature was heated to reflux
  3. temperaturewith reflux
  4. additionwas added
  5. stirringThe mixture was stirred for 4 hr
  6. customThe reaction solvent was removed in vacuo
  7. extractionA residue was extracted with Ethyl acetate
  8. washwashed with H2O and brine
  9. dry with materialdried with Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3af27ad2bc54ebcb78fe8b678041130
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

Loading…