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

HRID 1154562Notes

Reaction equation

HRID 1154562 reaction equation
[CH2:1]1[O:18][CH:4]([C:5]2[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]([O:14][CH3:15])[C:6]=2[O:16][CH3:17])[O:3][CH2:2]1.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.[Pt]=O>[CH2:2]1[O:3][CH:4]([C:5]2[C:6]([O:16][CH3:17])=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[NH2:11])[O:18][CH2:1]1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 13365013HCID 13365013, compound

Product 1

HCID 133650142-(1,3-Dioxolan-2-yl)-3,4-dimethoxyaniline

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,3-dimethoxy-6-nitrobenzaldehyde-ethyleneketal (12.1 g, 62.7 mM) in ethyl acetate (350 ml) containing sodium acetate (0.5 g) is treated with platinum oxide (1.0 g) and the mixture hydrogenated for 24 hours at ~50 psi. The solvent is removed in vacuo after filtering off the catalyst to give a pale brown oil. After crystallization from n-hexane, the product is obtained as a tan solid; yield 12.8 g (85.1%); m.p. 78°-80° C.

Workup

  1. customThe solvent is removed in vacuo
  2. filtrationafter filtering off the catalyst
  3. customto give a pale brown oil
  4. customAfter crystallization from n-hexane
  5. customthe product is obtained as a tan solid

Sources & evidence

ORD record
ord-0e96a93e67614489b2ea22f008954c3e
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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