Dimethyl Sulfate → Ethyl 4-amino-5-cyano-2-methoxybenzoate

HRID 846780Notes

Reaction equation

HRID 846780 reaction equation
[NH2:1][C:2]1[C:12]([C:13]#[N:14])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([OH:15])[CH:3]=1.S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(=O)C>[NH2:1][C:2]1[C:12]([C:13]#[N:14])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:15][CH3:20])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 3018374Ethyl 4-amino-5-cyano-2-hydroxybenzoate

Product 1

HCID 15096747Ethyl 4-amino-5-cyano-2-methoxybenzoateYield 79.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4.1 parts of ethyl 4-amino-5-cyano-2-hydroxybenzoate in 40 parts of 2-propanone were added successively 2.52 parts of dimethyl sulfate and 4.1 parts of potassium carbonate. The whole was stirred and refluxed for 3 hours. The reaction mixture was filtered while hot and the filter-cake was washed with 2-propanone. The filtrate was evaporated and the solid residue was crystallized from 24 parts of 2-propanol, yielding 3.5 parts (79.5%) of ethyl 4-amino-5-cyano-2-methoxybenzoate; mp. 164.5° C. (intermediate 110).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe reaction mixture was filtered while hot and the filter-cake
  3. washwas washed with 2-propanone
  4. customThe filtrate was evaporated
  5. customthe solid residue was crystallized from 24 parts of 2-propanol

Sources & evidence

ORD record
ord-f9f45f0c3fb647bb9be42a473f9ce78c
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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