Ammonia → Methyl 1-(aminocarbonyl)cyclopropanecarboxylate

HRID 866038Notes

Reaction equation

HRID 866038 reaction equation
[NH3:1].[C:2]1([C:9]([O:11][CH3:12])=[O:10])([C:5](OC)=[O:6])[CH2:4][CH2:3]1>CO>[NH2:1][C:5]([C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:3]1)=[O:6]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl ester

Product 1

HCID 11693923Methyl 1-(aminocarbonyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
8 °C

Procedure

Ammonia (20 l/h) is passed at 20° C. into a solution of 1,106 g (7 mol) of dimethyl cyclopropanedicarboxylate in 700 ml of methanol, with stirring. After approximately 10 hours, addition of NH3 is stopped, and the reaction mixture is cooled to 8° C. The solid formed is filtered off with suction, then washed using 200 g of cold methanol. After drying the product, 926.2 g (92.5%) of methyl 1-aminocarbonylcyclopropanecarboxylate are obtained (m.p.: 157° C.).

Workup

  1. customThe solid formed
  2. filtrationis filtered off with suction
  3. washwashed
  4. dry with materialAfter drying the product, 926.2 g (92.5%) of methyl 1-aminocarbonylcyclopropanecarboxylate
  5. customare obtained (m.p.: 157° C.)

Sources & evidence

ORD record
ord-795a2f93509444e1aa9699cb7b63d964
Source dataset
uspto-grants-1996_10
Patent number
US05569781

Reaction notes

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