Hydrochloric Acid → Methyl 4-(1-aminocyclopropyl)benzoate

HRID 72393

Reaction equation

HRID 72393 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH2:13]([Mg]Br)[CH3:14].B(F)(F)F.CCOCC.Cl>C(OCC)C.[Ti+4]>[NH2:2][C:1]1([C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 70791Methyl 4-cyanobenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 45140209Methyl 4-(1-aminocyclopropyl)benzoate

Reagents, catalysts & solvents 2

HCID 114942Titanium cation (4+)CatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To the solution of methyl 4-cyanobenzoate (100 g, 620 mmol) in diethyl ether (3 L) was added titanium (IV) isospropoxide (194 g, 682 mmol), followed by dropwise addition of ethylmagnesium bromide 3M solution in diethylether (450 ml, 1.36 mol) at −70° C. The mixture was stirred for 1 h, and then boron trifluoride etherate (157 ml, 1.24 mol) was added at once. After 2 hours, aqueous HCl (5%) was added until the pH showed acidy, then the mixture was filtered. The solid was washed with ethylacetate. The aqueous phase was separated and the organic layer was washed with water. All aqueous layers were collected together, basified with 1M NaOH and extracted with ethylacetate. The organic layer was dried (Na2SO4) and concentrated to afford the title compound (D6) (32.0 g).

Workup

  1. waitAfter 2 hours
  2. filtrationthe mixture was filtered
  3. washThe solid was washed with ethylacetate
  4. customThe aqueous phase was separated
  5. washthe organic layer was washed with water
  6. customAll aqueous layers were collected together
  7. extractionextracted with ethylacetate
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-69fbaee20a4b43819e198be7fc984b6b
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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