Hydrochloric Acid → 6-(Aminomethyl)picolinonitrile hydrochloride

HRID 2379793Notes

Reaction equation

HRID 2379793 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][C:10]2[N:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.[ClH:24]>CO.O1CCCC1>[ClH:24].[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 100383916-Phthalimidomethyl-2-pyridinecarbonitrile

Product 1

HCID 189539306-(Aminomethyl)picolinonitrile hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydrazine hydrate (0.77 g) in methanol (5 ml) was added dropwise to a suspension of 6-phthalimidomethyl-2-pyridinecarbonitrile (3.74 g) in a mixture of methanol (10 ml) and tetrahydrofuran (15 ml) at ambient temperature with stirring. After the mixture was stirred for two hours, diluted hydrochloric acid (prepared by concentrated hydrochloric acid (1.38 ml) and water (6.91 ml)) was dropped to the mixture. After stirring for three hours, the solvent was evaporated in vacuo. The residue was mixed with water (20 ml) and an insoluble material was filtered off. The filtrate was evaporated in vacuo to give 6-aminomethyl-2-pyridinecarbonitrile hydrochloride (2.40 g).

Workup

  1. stirringAfter the mixture was stirred for two hours
  2. stirringAfter stirring for three hours
  3. customthe solvent was evaporated in vacuo
  4. additionThe residue was mixed with water (20 ml)
  5. filtrationan insoluble material was filtered off
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-590f88ee3e064ceeb4d30449728c81f8
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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