2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (4-methoxy-2-nitrophenyl)-amide → 2-Isopropyl-5-methyl-cyclohexanecarboxylic (2-amino-4-methoxyphenyl)-amide

HRID 1914925Notes

Reaction equation

HRID 1914925 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH:12]2[CH2:17][CH:16]([CH3:18])[CH2:15][CH2:14][CH:13]2[CH:19]([CH3:21])[CH3:20])=[O:11])=[C:5]([N+:22]([O-])=O)[CH:4]=1>[Pd].C1COCC1.[OH-].[OH-].[Pd+2]>[NH2:22][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][C:10]([CH:12]1[CH2:17][CH:16]([CH3:18])[CH2:15][CH2:14][CH:13]1[CH:19]([CH3:21])[CH3:20])=[O:11]

Participants

5

Reactant 1

HCID 668315102-Isopropyl-5-methyl-cyclohexanecarboxylic acid (4-methoxy-2-nitrophenyl)-amide

Product 1

HCID 668315162-Isopropyl-5-methyl-cyclohexanecarboxylic (2-amino-4-methoxyphenyl)-amide

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolventHCID 23938PalladiumSolvent

Procedure

2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (4-methoxy-2-nitrophenyl)-amide (4.9 g) was dissolved in a suspension of 10% Pd—C (5 g) and THF (150 mL). The reaction mixture was hydrogenated over 20% Pd(OH)2 for 48 h with a balloon. The reaction mixture was filtered and concentrated to give the desired compound in sufficient purity to use in the next reaction without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-cdafb6e70778434fac67fcbb4a6912a6
Source dataset
uspto-grants-2013_12
Patent number
US08614243B2

Reaction notes

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