Acetic Acid → 1-(Quinolin-8-yl)ethan-1-amine

HRID 460148Notes

Reaction equation

HRID 460148 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7](N)[CH3:8])[CH:2]=1.[N:10]1[C:19]2[C:14](=CC=[CH:17][C:18]=2C(=O)C)C=CC=1.N.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[N:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:17][C:18]=2[CH:19]([NH2:10])[CH3:14])[CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 27716881-(Pyridin-3-yl)ethan-1-amineHCID 5003444Sodium cyanoborohydrideHCID 122087898-Acetylquinoline

Product 1

HCID 122087931-(Quinolin-8-yl)ethan-1-amineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by the same procedure for preparing 1-pyridin-3-yl-ethylamine from 1-quinolin-8-yl-ethanone (1.71 g, 10 mmol), 2 M ammonia solution in methyl alcohol, acetic acid (25 mL, 50 mmol, Aldrich) and sodium cyanoborohydride (2.5 g, 40 mmol, Aldrich). The title compound was purified by column chromatography (silica gel, ethyl acetate) in form as light yellow solid in 98% yield (1.68 g, 9.8 mmol). MS (ESI, pos. ion) m/z: 173.2 (M+1); MS (ESI, neg. ion) m/z: 171.0 (M−1).

Workup

  1. customThe title compound was purified by column chromatography (silica gel, ethyl acetate) in form as light yellow solid in 98% yield (1.68 g, 9.8 mmol)

Sources & evidence

ORD record
ord-6c88e2488ee445e799eac57301c7f3ce
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

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