Methanol → 2-Amino-4-butoxybenzoic acid methyl ester

HRID 72195Notes

Reaction equation

HRID 72195 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:20]O>CC(OC)(C)C>[CH3:20][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:10][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 202174402-Amino-4-butoxybenzoic acid

Product 1

HCID 689754012-Amino-4-butoxybenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of 2-amino-4-butoxybenzoic acid (2.0 g), thionyl chloride (1.2 g) and methanol (33 mL) was boiled under reflux for 24 hours. The reaction solution was diluted with MTBE and washed with sodium hydroxide solution. The organic phase was dried and concentrated. The product with the molecular weight of 223.27 (C12H17NO3) was obtained in this way; MS (ESI): 224 (M+H+).

Workup

  1. temperatureunder reflux for 24 hours
  2. washwashed with sodium hydroxide solution
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe product with the molecular weight of 223.27 (C12H17NO3) was obtained in this way

Sources & evidence

ORD record
ord-3a6f1e3e35b4485ba1d75418a662e72b
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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