Acetic Acid → HCID 58006241, compound

HRID 215929Notes

Reaction equation

HRID 215929 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1N.C=O.[BH3-][C:13]#[N:14].[Na+].[C:16](O)(=O)C>C(#N)C>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[N:14]([CH3:13])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 27562502-Bromo-6-methylanilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 58006241HCID 58006241, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-6-methylaniline (0.5 g, 2.69 mmol) in acetonitrile (30.0 mL) at ambient temperature was added a 37% aqueous solution of formaldehyde (4.0 mL, 53.6 mmol), followed by NaBH3CN (1.40 g, 22.1 mmol). The pH of the reaction was adjusted to pH 5-6 with glacial acetic acid, and the reaction was stirred for 4 h, then the solvent was removed. The residue was dissolved in EtOAc, and basified with NaOH 2N, dried over MgSO4, and filtered. The solvent was removed, and the residue was purified by silica gel flash chromatography with EtOAc (15%) and hexanes (85%) as eluent to produce Compound 150 as a clear oil.

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customthe residue was purified by silica gel flash chromatography with EtOAc (15%) and hexanes (85%) as eluent

Sources & evidence

ORD record
ord-0cc869149c394467b08ec36a54eb2dd9
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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