Acetic Acid → 3-Amino-4-methoxyphenyl ethyl carbonate

HRID 1776587Notes

Reaction equation

HRID 1776587 reaction equation
[C:1](=[O:17])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N+:14]([O-])=O)[CH:7]=1)[O:2][CH2:3][CH3:4].C(O)(=O)C>CCOC(C)=O.[Pd]>[C:1](=[O:17])([O:2][CH2:3][CH3:4])[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([NH2:14])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86679539Ethyl 4-methoxy-3-nitrophenyl carbonate

Product 1

HCID 134556543-Amino-4-methoxyphenyl ethyl carbonateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-methoxy-3-nitrophenyl carbonate (0.720 g, 2.99 mmol) was dissolved in EtOAc (20 ml), and glacial acetic acid (0.200 ml, 3.49 mmol) was added followed by 10% palladium on carbon (0.100 g, 0.094 mmol). The mixture was stirred in a Parr apparatus under hydrogen atmosphere (25 psi) for 2 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The resulting crude 3-amino-4-methoxyphenyl ethyl carbonate (0.600 g, 2.84 mmol, 95% yield, MS/ESI+ 212.3 [MH]+), was used for the next step without any further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-62a3e974e4604c02bc81588776331c5b
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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