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

HRID 2113125Notes

Reaction equation

HRID 2113125 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-7a5d970e59d54734bacd93471f4ce7da
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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