Chlorotrimethylsilane → Methyl 2-(3-aminophenyl)acetate hydrochloride

HRID 15815

Reaction equation

HRID 15815 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:12][Si](C)(C)[CH3:14]>CO>[ClH:12].[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:14])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 44119610Methyl 2-(3-aminophenyl)acetate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

3-Aminophenylacetic acid (1 wt) was suspended in methanol (5 vol) under nitrogen at 20° C. Chlorotrimethylsilane (1.26 vol) was added over 60 minutes at 20° C. The reaction mixture was stirred at 20° C. for one hour, then concentrated under reduced pressure to 3 vol. Methyl-t-butyl ether (4 vol) was added and the resulting suspension was stirred at room temperature for 18 hours. The solid was collected by filtration, washing with methyl-t-butyl ether (4×1 vol). The material was dried in oven at 40° C. for 5 hours to give the title compound.

Workup

  1. concentrationconcentrated under reduced pressure to 3 vol. Methyl-t-butyl ether (4 vol)
  2. additionwas added
  3. stirringthe resulting suspension was stirred at room temperature for 18 hours
  4. filtrationThe solid was collected by filtration
  5. washwashing with methyl-t-butyl ether (4×1 vol)
  6. customThe material was dried in oven at 40° C. for 5 hours

Sources & evidence

ORD record
ord-4e29d29479dd4036a2642dc99786f17a
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Linked notes

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