Acetic Acid → HCID 58154530, compound

HRID 2359400Notes

Reaction equation

HRID 2359400 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][CH2:19][C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 103713-PyridinecarboxaldehydeHCID 3465192-Chloroquinolin-8-amineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 58154530HCID 58154530, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-chloroquinolin-8-amine (1.75 g, 9.8 mmol), 3-pyridinecarbaldehyde (2.14 g, 20 mmol) and AcOH (1.2 g, 20 mmol) in MeOH (10 mL) were added NaCNBH3 (1.26 g, 20 mmol) in portions at room temperature, then the reaction mixture was stirred at room temperature for 5 h. The reaction was concentrated in vacuo, and the residue was taken up in CH2Cl2. The solution was washed with water (1×50 mL), dried over Na2SO4, concentrated and purified by silica gel column (20:1 pentane/ethyl acetate) to give 2-chloro-N-(pyridin-3-ylmethyl)quinolin-8-amine as a yellow oil (2.1 g, yield 80%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washThe solution was washed with water (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column (20:1 pentane/ethyl acetate)

Sources & evidence

ORD record
ord-569de94d215547e6b79f80d86f08beed
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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