4-Hydroxy-3-nitrobenzaldehyde → 1-(2,2-Dimethoxyethyl)-3-amino-4-octyloxybenzene

HRID 128781

Reaction equation

HRID 128781 reaction equation
[N+](C1C=C(C=CC=1O)C=O)([O-])=O.[CH3:13][O:14][CH:15]([O:35][CH3:36])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:19]([N+:32]([O-])=O)[CH:18]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:36][O:35][CH:15]([O:14][CH3:13])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:19]([NH2:32])[CH:18]=1

Participants

6

Reactant 3

HCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 2723923Ammonium formateHCID 193751161-(2,2-Dimethoxyethyl)-3-nitro-4-octyloxybenzene

Product 1

HCID 193751221-(2,2-Dimethoxyethyl)-3-amino-4-octyloxybenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

By the method of example 1 above, 3-nitro-4-hydroxybenzaldehyde is converted into 1-(2,2-dimethoxyethyl)-3-nitro-4-octyloxybenzene. This material (1.83 g) is dissolved in ethanol (20 ml) and to the solution is added ammonium formate (3.5 g) and palladium black (0.30 g), and the mixture is stirred for 30 min. The mixture is filtered through diatomaceous earth and evaporated to dryness in vacuo. The residue is partitioned between water and dichloromethane, and the organic phase is dried over magnesium sulfate, filtered, and concentrated to give 1-(2,2-dimethoxyethyl)-3-amino-4-octyloxybenzene as an orange oil (1.64 g, 98%).

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. customevaporated to dryness in vacuo
  3. customThe residue is partitioned between water and dichloromethane
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd0c548b86e84427b7445ce0a434b603
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Linked notes

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