Methanol → Methyl 4-(1-aminocyclopropyl)benzoate

HRID 1466405Notes

Reaction equation

HRID 1466405 reaction equation
[NH2:1][C:2]1([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.CO.[CH3:16][Si](C=[N+]=[N-])(C)C.CCCCCC>C1COCC1>[NH2:1][C:2]1([C:5]2[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:16])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 451402084-(1-Aminocyclopropyl)benzoic acid

Product 1

HCID 45140209Methyl 4-(1-aminocyclopropyl)benzoateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-aminocyclopropyl)benzoic acid (1.75 g, 0.00988 mol) was stirred in THF (20 mL) and Methanol (10 mL) over ice/water bath. 2.00 M of trimethylsilyldiazomethane in hexane (9.9 mL, 0.020 mol) was added and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated down to viscous oil which solidified upon standing to give a crystalline solid. Crude material was dried on high vacuum line for 12 hours to give methyl 4-(1-aminocyclopropyl)benzoate (1.65 g, 87%) as pale brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated down to viscous oil which
  2. customto give a crystalline solid
  3. customCrude material was dried on high vacuum line for 12 hours

Sources & evidence

ORD record
ord-7407d88d941c48b0880db251dbbbc6b4
Source dataset
uspto-grants-2015_04
Patent number
US09000024B2

Reaction notes

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