Isopropanol → 3-Methoxy-5-(propan-2-yloxy)aniline

HRID 1616945Notes

Reaction equation

HRID 1616945 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH:11]([OH:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:11]([O:14][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1)[NH2:1])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 119535163-Amino-5-methoxyphenol

Product 1

HCID 115719053-Methoxy-5-(propan-2-yloxy)anilineYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-5-methoxyphenol (5.44 g, 39.1 mmol), isopropyl alcohol (3.6 ml, 47 mmol) and triphenylphosphine (12.0 g, 47 mmol) in THF, was added diethyl azodicarboxylate (7.4 ml, 47 mmol). The reaction mixture was stirred for 16 h and the solvent was removed. The residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes to afford the title compound (4.13 g). MS m/z: 182 [M+H]+

Workup

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-689972f5ed864150a37c67ba9247ea6a
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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