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

HRID 1250064Notes

Reaction equation

HRID 1250064 reaction equation
[C:1]([O:4][C:5]1[C:23]([O:24][CH3:25])=[CH:22][C:8]([C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[O:10])=[CH:7][C:6]=1[O:26][CH3:27])(=[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:23]([O:24][CH3:25])=[CH:22][C:8]([C:9]([NH:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)=[O:10])=[CH:7][C:6]=1[O:26][CH3:27])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 219185543,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamideHCID 219186094-acetoxy-3,5-dimethoxy-N-[(4-nitrophenyl)methyl]-benzamide

Product 1

HCID 219187394-acetoxy-3,5-dimethoxy-N-[(4-aminophenyl)methyl]-benzamideYield 82%

Procedure

The experimental protocol used is the same as that described for intermediate 2.2, 4-acetoxy-3,5-dimethoxy-N-[(4-nitrophenyl)methyl]-benzamide replacing the 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamide. A colourless oil is obtained with a yield of 82%. The product is used directly in the following stage without additional purification.

Workup

  1. customA colourless oil is obtained with a yield of 82%
  2. customThe product is used directly in the following stage without additional purification

Sources & evidence

ORD record
ord-ff935bcfadc84cd890e79cb1ece08699
Source dataset
uspto-grants-2002_01
Patent number
US06335445B1

Reaction notes

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