1-Chloro-2-nitrobenzene → HCID 21875993, compound

HRID 967844Notes

Reaction equation

HRID 967844 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=1>>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 669044-Aminophenethyl alcohol

Product 1

HCID 21875993HCID 21875993, compoundYield 55%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloronitrobenzene (3.9 g, 25 mmol) and 4-aminophenylethyl alcohol (4.1 g, 30 mmol) was placed in a sealed tube and heated at 150° C. for 3 h. The reaction mixture was cooled and purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1) to afford 3.5 g (55%) of the title compound as orange solids: 1H-NMR (CDCl3)δ2.90 (2H, t, J=6.5 Hz), 3.91 (2H, t, J=6.5 Hz), 6.81-6.70 (1H, m), 7.40-7.16 (6H, m), 8.21 (1H, dd, J=1.5, 8.8 Hz), 9.47 (1H, s).

Workup

  1. customwas placed in a sealed tube
  2. temperatureThe reaction mixture was cooled
  3. custompurified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-c552b29062b24855b07ce011991cd391
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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