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

HRID 393842Notes

Reaction equation

HRID 393842 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([OH:23])[C:21]=1[OH:22])[C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)=[O:6].CC(C1C=C(C=C(C(C)(C)C)C=1O)C(NCC1C=CC([N+]([O-])=O)=CC=1)=O)(C)C>>[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([OH:23])[C:21]=1[OH:22])[C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)=[O:6]

Participants

3

Reactant 2

HCID 219185543,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamideHCID 219187493,4,5-trihydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide

Product 1

HCID 219187373,4,5-trihydroxy-N-[2-(4-aminophenyl)ethyl]-benzamideYield 89%

Procedure

The experimental protocol used is the same as that described for intermediate 2.2, with 3,4,5-trihydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide replacing the 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamide. A beige powder is obtained with a yield of 89%. Melting point: 167-169° C.

Workup

  1. customA beige powder is obtained with a yield of 89%

Sources & evidence

ORD record
ord-921f0481360e47c6a744318088a6046c
Source dataset
uspto-grants-2004_10
Patent number
US06809088B2

Reaction notes

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