Water → (6-Chloro-5-methylpyridin-3-yl)methanamine hydrochloride

HRID 711238Notes

Reaction equation

HRID 711238 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([Cl:11])=[N:9][CH:10]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[ClH:11].[Cl:11][C:8]1[N:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866797195-(Azidomethyl)-2-chloro-3-methylpyridine

Product 1

HCID 53395592(6-Chloro-5-methylpyridin-3-yl)methanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 5-(azidomethyl)-2-chloro-3-methylpyridine 30-3 (2.0 g, 11 mmol) in THF (20 mL) was added PPh3 (3.17, 12 mmol) slowly. After 2 hours, H2O was added to the reaction mixture and the reaction was stirred for additional 15 hours, and the solvent was removed. The crude product was partitioned between ethyl acetate (50 mL) and 0.2 N HCl (50 mL). The aqueous phase was dried to give (6-chloro-5-methylpyridin-3-yl)methanamine HCl salt 30-4 as a white solid.

Workup

  1. customthe solvent was removed
  2. customThe crude product was partitioned between ethyl acetate (50 mL) and 0.2 N HCl (50 mL)
  3. customThe aqueous phase was dried

Sources & evidence

ORD record
ord-ef5dfc70a84f455cb88af2762191b626
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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