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

HRID 1094118Notes

Reaction equation

HRID 1094118 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).

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)

Sources & evidence

ORD record
ord-780da1b8b73a4ffbb636ae612279175d
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

Loading…