Acetic Acid → 4-Chloro-N,N-dimethylpyridin-2-amine

HRID 2361641Notes

Reaction equation

HRID 2361641 reaction equation
[C:1](O)(=O)C.N[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][N:7]=1.C=O.[BH3-][C:16]#[N:17].[Na+].[OH-].[Na+]>CC#N.O>[Cl:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([N:17]([CH3:16])[CH3:1])[CH:11]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5818662-Amino-4-chloropyridineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 121751354-Chloro-N,N-dimethylpyridin-2-amineYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetic acid (0.6 ml, 10.5 mmol) was added dropwise to a solution of 2-amino-4-chloropyridine (384 mg, 3.0 mmol), formaldehyde (2.4 ml of a 37% aqueous solution, 29.6 mmol) and NaBH3CN (581 mg, 9.0 mmol) in MeCN (10 ml) and water (2 ml) at 0° C. After 10 minutes the reaction was warmed to room temperature and stirred for 3 days. The reaction was basified to pH4 with 1M aq. NaOH and then extracted with diethyl ether (3×30 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (Hexane/Diethyl ether with gradient, 98:2 to 8:2) to provide the title compound as colourless oil (260 mg, 56%).

Workup

  1. extractionextracted with diethyl ether (3×30 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by FCC (Hexane/Diethyl ether with gradient, 98:2 to 8:2)

Sources & evidence

ORD record
ord-3ffa04acc09a4f7b8453713428f5b7a7
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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