Acetic Acid → HCID 12419118, compound

HRID 2271651Notes

Reaction equation

HRID 2271651 reaction equation
N[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].C=O.[C:16]([BH3-])#[N:17].[Na+].[C:20](O)(=O)C>CO>[CH3:20][N:17]([CH3:16])[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[OH:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 408542HCID 408542, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12419118HCID 12419118, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-1-(4-nitrophenyl)ethanone (500 mg, 2.30 mmol), paraformaldehyde (207 mg, 6.90 mmol), and sodium cyanoborohydride (433 mg, 6.90 mmol) in methanol (30 mL) was added acetic acid (catalytic) and the reaction stirred at room temperature for 18 h. The reaction mixture was quenched with water and the layers were separated. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated, and chromatographed (CH2Cl2/MeOH) to afford the desired product (164 mg, 34%) as an orange oil: ESI MS m/z 211 [C10H14N2O3+H]+.

Workup

  1. customThe reaction mixture was quenched with water
  2. customthe layers were separated
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-a8e055c8d80b4c55b66139c6fb5c35a3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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