Butanoic acid, 4-chloro-4-oxo-, ethyl ester → HCID 57426203, compound

HRID 551045Notes

Reaction equation

HRID 551045 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].[Cl-].C[Al+]C.Cl[C:18](=[O:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:18](=[O:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][NH:8]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 1457664-Nitro-1H-indoleHCID 16686359Dimethylalumanylium chloride

Product 1

HCID 57426203HCID 57426203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-nitroindole (2.00 g, 12.3 mmol) in CH2Cl2 (60 mL) at 0° C. was added dimethylaluminum chloride (1 M in hexanes, 14.8 mL, 14.8 mmol) and the mixture was stirred for 30 min. Ethyl 4-chloro-4-oxobutyrate (2.44 g, 14.8 mmol) was added dropwise and the resulting mixture was allowed to warm slowly to ambient temperature and stirred for 18 h. The reaction mixture was carefully quenched with 10% aqueous citric acid (150 mL) and extracted with CH2Cl2 (3×150 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was partially purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 65:35, and the resulting crude product was recrystallized from CH2Cl2:MeOH to give the title compound. MS: m/z=291 (M+1).

Workup

  1. stirringstirred for 18 h
  2. customThe reaction mixture was carefully quenched with 10% aqueous citric acid (150 mL)
  3. extractionextracted with CH2Cl2 (3×150 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was partially purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2
  9. customEtOAc—100:0 to 65:35, and the resulting crude product was recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-aa272e042d5e489ebb097657be1a3278
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

Loading…