2-Bromo-4-isopropylaniline → HCID 18427729, compound

HRID 1279263Notes

Reaction equation

HRID 1279263 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11]C(CCC)CCC)[CH:5]=[C:4]([CH3:19])[N:3]=1.[Br:20][C:21]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[CH:24][C:22]=1[NH2:23]>C(Cl)Cl>[Br:20][C:21]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[CH:24][C:22]=1[N:23]([CH:21]([CH2:27][CH2:26][CH3:28])[CH2:22][CH2:24][CH3:25])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([CH3:19])[N:3]=1

Participants

4

Reactant 2

HCID 5213372-Bromo-4-isopropylanilineHCID 11403413HCID 11403413, compound

Product 1

HCID 18427729HCID 18427729, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-6-methyl-3-nitro-N-(1-propylbuty)pyridin-4-amine (0.5 g, 1.75 mmol) and 2-bromo-4-isopropylaniline (0.74 g, 3.5 mmol) were heated at 140° C. for 4.5 h. After cooling it was dissolved in CH2Cl2 and filtered through a short column of silica gel. The filtrate was concentrated and chromatographed on silica gel (5% EtOAc/hexanes eluting solvent) to give the product (0.7 g).

Workup

  1. temperatureAfter cooling it
  2. filtrationfiltered through a short column of silica gel
  3. concentrationThe filtrate was concentrated
  4. customchromatographed on silica gel (5% EtOAc/hexanes eluting solvent)

Sources & evidence

ORD record
ord-70ae32cd4dd84cc5ae9f5977be46ec74
Source dataset
uspto-grants-2002_09
Patent number
US06448261B1

Reaction notes

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