Hydrochloric Acid → Ethyl 2-[3-(methylamino)phenyl]acetate

HRID 1383361Notes

Reaction equation

HRID 1383361 reaction equation
B.CSC.[CH2:5]([O:7][C:8](=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH:17]=O)[CH:11]=1)[CH3:6].Cl>C1COCC1>[CH2:5]([O:7][C:8](=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH3:17])[CH:11]=1)[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 542316283-(Formylamino)phenylacetic acid ethyl ester

Product 1

HCID 23333594Ethyl 2-[3-(methylamino)phenyl]acetateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane-dimethylsulphide complex (2M in THF; 20 mL) was added to an ice cold solution of 3-(formylamino)phenylacetic acid ethyl ester (4.1 g; 0.02 mol; from step (i) above) in THF (dry; 100 mL) and the reaction mixture was stirred for 1 hour. The resultant solution was poured onto diluted HCl and the mixture left for 15 minutes, whereafter it was washed with ether to remove unreacted material. The aqueous solution was made alkaline (NaHCO3) and extracted with ether (3 times). The combined organic phases were washed with water, dried (Na2SO4) and evaporated to yield 3.0 g (78%) of the sub-title compound.

Workup

  1. waitthe mixture left for 15 minutes, whereafter it
  2. washwas washed with ether
  3. customto remove unreacted material
  4. extractionextracted with ether (3 times)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-c5a8e57bd9ff4f2cb917f594c7571d6a
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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