4-Chloro-2-methoxy-5-(prop-1-en-2-yl)benzenamine → 4-Chloro-5-isopropyl-2-methoxybenzenamine

HRID 588878Notes

Reaction equation

HRID 588878 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([CH3:10])=[CH2:9])=[CH:6][C:5]([NH2:11])=[C:4]([O:12][CH3:13])[CH:3]=1>CO.[Ni]>[Cl:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([NH2:11])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

4

Reactant 1

HCID 904593934-Chloro-2-methoxy-5-(prop-1-en-2-yl)benzenamine

Product 1

HCID 1176071904-Chloro-5-isopropyl-2-methoxybenzenamineYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-2-methoxy-5-(prop-1-en-2-yl)benzenamine (160 mg, 0.81 mmol), Raney-Ni (20 mg) in MeOH (5 mL) was stirred at RT under H2 (1 atm) atmosphere for 8 h. The mixture was filtered and the filtrate was concentrated in vacuo to afford the desired product (150 mg, 93% yield).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4815e61dd847421d91c841ffe3f47465
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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