Hydrochloric Acid → (5-Bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine hydrochloride

HRID 623508Notes

Reaction equation

HRID 623508 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[ClH:26]>O1CCOCC1>[ClH:26].[Br:1][C:2]1[CH:3]=[C:4]([CH2:14][NH2:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 675085372-((5-Bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 67508543(5-Bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Free base of the title compound is prepared in 97% yield (510 mg, clear colorless oil) from 2-((5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione (770 mg, 1.8 mmol, Step-2) by the similar manner in Step-4 of Amine-24. The obtained amine is suspended in 4M hydrochloric acid in dioxane (3 mL), and the mixture is stirred for 30 minutes at room temperature to give a white precipitate. The precipitate is collected by filtration, washed with dichloromethane, dried in vacuo to give 540 mg (94% yield) of the title compound as a white solid.

Workup

  1. customto give a white precipitate
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with dichloromethane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3a8f0d95c460408698dc3ba9d60f33d0
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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