Water → Methyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 1476057Notes

Reaction equation

HRID 1476057 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][C:15]([O:17][C:18](C)(C)C)=[O:16])[CH:9]=[CH:10][C:11]=1[Cl:12].O>CO.ClCCl>[NH2:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 58136497Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

Product 1

HCID 58288398Methyl 3-(3-amino-4-chlorophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Under reflux, 0.86 ml (11.7 mmol) of thionyl chloride was added dropwise to a solution of 1.0 g (3.91 mmol) of tert-butyl 3-(3-amino-4-chlorophenyl)propanoate in 20 ml of methanol. The mixture was stirred under reflux for 1.5 h and then, after cooling, diluted with dichloromethane. The solution was added to water, and after phase separation the organic phase was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The residue was dried under high vacuum. This gave 745 mg (90.3% of theory) of the target compound.

Workup

  1. temperatureUnder reflux
  2. temperatureunder reflux for 1.5 h
  3. temperatureafter cooling
  4. customafter phase separation the organic phase
  5. washwas washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-9bbfc1e6805845f7bebf83cf1c138514
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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