Ammonium Hydroxide → 5-(Aminomethyl)pyridin-2-amine

HRID 2076244Notes

Reaction equation

HRID 2076244 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.B.C1COCC1.[NH4+].[OH-]>Cl>[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 8182602-Amino-5-cyanopyridineHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 157667715-(Aminomethyl)pyridin-2-amineYield 83.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 6-aminonicotinonitrile 117-A (5.0 g, 42 mmol) was added a solution of 1 M BH3-THF (294 mL, 294 mmol) at 0° C. (prepared as in J. Org. Chem., Vol. 38, No. 5, 1973). The reaction was stirred at room temperature for 1 hour. The reaction mixture was then slowly pored into ice water. 100 mL 4N HCl was added and stirred for 20 min. The solution was basified with NH4OH to pH of about 11, and then concentrated. THF (300 mL×2) was added to the mixture followed by addition of solid KOH (excess). The suspension was stirred. The THF layer was collected by filtration and concentrated to give 5-(aminomethyl)pyridin-2-amine 117-B (4.3 g).

Workup

  1. customprepared as in J
  2. stirringstirred for 20 min
  3. concentrationconcentrated
  4. additionTHF (300 mL×2) was added to the mixture
  5. additionfollowed by addition of solid KOH (excess)
  6. stirringThe suspension was stirred
  7. filtrationThe THF layer was collected by filtration
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c2725a52dd214843bff0325610f4900c
Source dataset
uspto-grants-2011_04
Patent number
US07923457B2

Reaction notes

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