Methanol → HCID 67244427, compound

HRID 2358381Notes

Reaction equation

HRID 2358381 reaction equation
[NH2:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1Cl.[CH3:12]O>C1COCC1>[NH2:7][CH2:6][C:5]1[CH:4]=[C:3]([CH3:12])[C:2]([NH2:1])=[C:9]([I:10])[CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 26598361HCID 26598361, compound

Product 1

HCID 67244427HCID 67244427, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-3-chloro-5-iodobenzonitrile (65.2 mg, 0.23 mmol) was dissolved in THF at 0° C. After Borane-THF complex (4 eq, 0.94 mmol, 0.94 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-methyl-phenylamine (19.4 mg).

Workup

  1. additionAfter Borane-THF complex (4 eq, 0.94 mmol, 0.94 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-1840eb2adc334a0fad512ed5a222e3c5
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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