Acetic Acid → HCID 43194183, compound

HRID 2043328Notes

Reaction equation

HRID 2043328 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][C:10]([CH:12]1[CH2:14][CH2:13]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH:10]([CH:12]2[CH2:14][CH2:13]2)[CH3:9])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 79323-ChloroanilineHCID 13004Cyclopropyl methyl ketoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43194183HCID 43194183, compoundYield 4.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloroaniline (1.27 g, 10 mmol) in 1,2-dichloroethane (20 ml) were added molecular sieves (4 g, size 0.4 nM) and cyclopropyl methyl ketone (0.84 g, 10 mmol). After stirring the mixture for 5 min at room temperature sodium triacetoxyborohydride (3.18 g, 15 mmol) and acetic acid (0.6 g, 10 mmol) were added. The reaction mixture was stirred at room temperature overnight. For workup dichloromethane (100 ml) and 1 M sodium bicarbonate solution (40 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=9:1) to yield a colourless liquid (0.083 g, 4.5%); MS (ISP): 196.3 (M+H)+.).

Workup

  1. additionwere added
  2. stirringthe mixture was shaken
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-83197a489631467d93422a60dbff99ab
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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