Sodium Acetate → 2-(1,3-Dioxolan-2-yl)-4-methoxyaniline

HRID 639352Notes

Reaction equation

HRID 639352 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[N+:14]([O-])=O.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.[Pt]=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[NH2:14]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 572490272-(5-Methoxy-2-nitrophenyl)-1,3-dioxolane

Product 1

HCID 153389082-(1,3-Dioxolan-2-yl)-4-methoxyaniline

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(1,3-dioxolan-2-yl)-4-methoxy-1-nitrobenzene (1eq) in ethyl acetate was treated with sodium acetate (0.08eq) and platinum oxide (0.06eq) and hydrogenated in a Parr apparatus at 50 psi for 16 hours. The reaction mixture was filtered and the filtrate was concentrated to give 2-(1,3-dioxolan-2yl)-4-methoxyphenylamine in quantitative yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4acf5e206270489eb1fa7a8ca652d9a3
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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