3,4-Dichloroaniline → HCID 57733347, compound

HRID 1920759Notes

Reaction equation

HRID 1920759 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[O:6][C:5]=1[NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])(=O)[CH3:2].[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[Cl:33])[NH2:29]>C(#N)C>[C:19]1([C@@H:16]([NH:15][C:5]([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[N:29]([C:28]3[CH:30]=[CH:31][C:32]([Cl:33])=[C:26]([Cl:25])[CH:27]=3)[C:1]=2[CH3:2])=[O:6])[CH2:17][CH3:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 57733336HCID 57733336, compound

Product 1

HCID 57733347HCID 57733347, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-acetyl-3-((S)-1-phenyl-propylamino)-isochromen-1-one (60 mg) and 3,4-dichloroaniline (250 mg) in acetonitrile (0.5 ml) were heated under microwave irradiation at 160° C. for 15 min. The reaction mixture was partitioned between 2M HCl (3 ml) and ethyl acetate (3 ml). The organic solution was absorbed on SiO2 (600 mg) and flash chromatographed on SiO2 (20 g) with gradient heptane-ethyl acetate to give 22 mg of the title compound as a white solid. LC-MS (m/z) 465.4 & 467.4 (MH+); tR=1.63.

Workup

  1. customThe reaction mixture was partitioned between 2M HCl (3 ml) and ethyl acetate (3 ml)
  2. customThe organic solution was absorbed on SiO2 (600 mg) and flash
  3. customchromatographed on SiO2 (20 g) with gradient heptane-ethyl acetate

Sources & evidence

ORD record
ord-83fa3438494847d0a9fd74ce79b3a8a1
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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