Formaldehyde → HCID 919489, compound

HRID 1520163Notes

Reaction equation

HRID 1520163 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7](N)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]=O.[BH3-][C:15]#[N:16].[Na+]>CO.O>[CH3:12][N:16]([CH3:15])[C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 113736-AminoquinolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 919489HCID 919489, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of quinolin-6-amine (666 mg, 4.62 mmol) in CH3OH (15 ml) was added 40% aqueous formaldehyde (1 ml), NaBH3CN (400 mg, 6.37 mmol) with stirring for 3 days at room temperature and diluted with water (150 ml), extracted with ethyl acetate (3×30 ml), dried over magnesium sulfate and concentrated in vacuo to give a residue, which was purified by a silica gel column chromatography with 5%-20% ethyl acetate in petroleum ether to give N,N-dimethylquinolin-6-amine as a solid (400 mg, 50%).

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by a silica gel column chromatography with 5%-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-71f258dac5ad4abda7efe87b04241fe9
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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