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

HRID 128781

반응식

HRID 128781 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dd0c548b86e84427b7445ce0a434b603
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

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