tert-butyl N-(2-methoxyphenyl)carbamate → 2-Methoxyaniline

HRID 1292838Notes

Reaction equation

HRID 1292838 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH2:7]

Participants

3

Reactant 2

HCID 4935494tert-butyl N-(2-methoxyphenyl)carbamateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 70002-MethoxyanilineYield 16.1%

Procedure

0.35 g of tert-butyl-N-(2-methoxyphenyl)carbamate (theoretically 2 mmol/g) bonded on solid support 8 is reacted with 0.5 ml (7 mmol, 10 eq) of a 20% solution of TFA/CH2Cl2 at room temperature for 1 hour. The resin is filtered on a scintered filter and rinsed with CH2Cl2 and MeOH. Then, the filtrate is concentrated under vacuum, taken up in CH2Cl2, washed with a saturated aqueous NaHCO3 solution. After drying on MgSO4 and evaporation of the solvent, 31.1 mg of 2-methoxyaniline is obtained and characterized by the 1H NMR spectrum and compared with the commercial product (yield: 36%). An IR control of the resin showed that the cleavage was not complete (presence of a carbonyl band at 1729 cm−1). The resin was then reacted again with 10 equivalents of a 20% solution of TFA/CH2Cl2 for 15 hours at room temperature. After an identical treatment, 13.8 g of pure 2-methoxyaniline were obtained (overall yield: 52%).

Workup

  1. filtrationThe resin is filtered on
  2. filtrationa scintered filter
  3. washrinsed with CH2Cl2 and MeOH
  4. concentrationThen, the filtrate is concentrated under vacuum
  5. washwashed with a saturated aqueous NaHCO3 solution
  6. customAfter drying on MgSO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-e7b0623fba3a459fb4d6334ac7b64305
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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