3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamide → 4-acetoxy-3,5-dimethoxy-N-[2-(4-aminophenyl)ethyl]-benzamide

HRID 987017Notes

Reaction equation

HRID 987017 reaction equation
[C:1]([O:4][C:5]1[C:24]([O:25][CH3:26])=[CH:23][C:8]([C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)=[O:10])=[CH:7][C:6]=1[O:27][CH3:28])(=[O:3])[CH3:2].CC(C1C=C(C=C(C(C)(C)C)C=1O)C(NCC1C=CC([N+]([O-])=O)=CC=1)=O)(C)C>>[C:1]([O:4][C:5]1[C:24]([O:25][CH3:26])=[CH:23][C:8]([C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)=[O:10])=[CH:7][C:6]=1[O:27][CH3:28])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 219185543,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamideHCID 219187614-acetoxy-3,5-dimethoxy-N-[2-(4-nitrophenyl)ethyl]-benzamide

Product 1

HCID 219187474-acetoxy-3,5-dimethoxy-N-[2-(4-aminophenyl)ethyl]-benzamide

Procedure

The experimental protocol used is the same as that described for intermediate 2.2, with 4-acetoxy-3,5-dimethoxy-N-[2-(4-nitrophenyl)ethyl]-benzamide replacing the 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamide. A colourless oil is obtained with a quantitative yield. The product is used directly in the following stage without additional purification.

Workup

  1. customA colourless oil is obtained with a quantitative yield
  2. customThe product is used directly in the following stage without additional purification

Sources & evidence

ORD record
ord-329f0f8905fc45e1bfd311c9123dd848
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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