Methanol → 3-(Aminomethyl)-5-chloroaniline

HRID 917537Notes

Reaction equation

HRID 917537 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[C:5]#[N:6].CO>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 110300243-Amino-5-chlorobenzonitrile

Product 1

HCID 134650993-(Aminomethyl)-5-chloroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-amino-5-chlorobenzonitrile in THF at RT was added slowly borane methyl sulfide complex (2.5 eq.). The resulting reaction mixture was stirred at RT for 1 h and heated at reflux for 2 hrs. The reaction mixture was cooled to −30° C. and MeOH was added slowly to quench the reaction. Solvent was evaporated in vacuo after the reaction mixture was stirred at RT for 30 min. to give 3-amino-5-chlorobenzylamine, which was used without purification. LCMS (Method A) RT 0.16 min., MH+ 157.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureat reflux for 2 hrs
  4. temperatureThe reaction mixture was cooled to −30° C.
  5. customto quench
  6. customthe reaction
  7. customSolvent was evaporated in vacuo after the reaction mixture
  8. stirringwas stirred at RT for 30 min.

Sources & evidence

ORD record
ord-162fae0daacc4c3b9512815950f55d7f
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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