2-Chloro-6-methyl-4-nitroaniline → HCID 67406977, compound

HRID 1783356Notes

Reaction equation

HRID 1783356 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[NH2:12].[CH:13]1([CH2:18][C:19](Cl)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[NH:12][C:19](=[O:20])[CH2:18][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 27334602-Chloro-6-methyl-4-nitroanilineHCID 3485182Cyclopentylacetyl chloride

Product 1

HCID 67406977HCID 67406977, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-6-methyl-4-nitro-phenylamine (6.0 g) and cyclopentylacetyl chloride (5.1 g) were dissolved in acetonitrile (45 mL) and heated to 150° C. for 20 minutes in a sealed microwave process vessel. The reaction mixture was cooled to 0° C. and the precipitated product collected by filtration and washed with cold acetonitrile to furnish 5.5 g (58%) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 1.24 (m, 2H), 1.58 (m, 4H), 1.78 (m, 2H), 2.27 (m, 1H), 2.30 (s, 3H), 2.38 (d, 2H), 8.15 (d, 1H), 8.18 (d, 1H), 9.83 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe precipitated product collected by filtration
  3. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-043fdd206af64f83ba1b370e4f747c34
Source dataset
uspto-grants-2009_03
Patent number
US07501414B2

Reaction notes

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