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

HRID 128781

反応式

HRID 128781 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-dd0c548b86e84427b7445ce0a434b603
出典データセット
uspto-grants-1995_11
特許番号
US05464865

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