Dimethylformamide → ethyl 2-((3-((hydroxyimino)methyl)-1H-indol-5-yl)oxy)acetate

HRID 68324Notes

Reaction equation

C[N:2]([CH:4]=O)[CH3:3].P(Cl)(Cl)(Cl)=[O:7].[NH:11]1C2[C:14](=[CH:15][C:16]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1>ClC(Cl)C>[OH:7][N:11]=[CH:12][C:13]1[C:14]2[C:3](=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:15]=2)[NH:2][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To DMF (1.74 gm, 0.023 moles) cooled to 0° C. under nitrogen atmosphere, Phosphorous oxy chloride (3.5 gm, 0.022 moles) was added in portions and stireed for 15 mins. To this was added a solution of the product of step 1 (2.5 gm, 0.011 mole) in dichloro ethane (18 ml) at 0° C. and heated to 80° C. for 2 hrs. The solvents were evaporated under reduced pressure. The residue was dissolved in water, basified with NaOH and extracted with ethyl acetate. The ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography (eluent: 40% EtOAC in hexane) to yield 900 mg (31%) of product as solid.

Workup

customThe solvents were evaporated under reduced pressure
dissolutionThe residue was dissolved in water
extractionextracted with ethyl acetate
extractionThe ethyl acetate extract
washwas washed with water & brine
dry with materialdried over sodium sulphate
customevaporated under reduced pressure
customThe crude product was purified by column chromatography (eluent: 40% EtOAC in hexane)

Sources & evidence

ORD record: ord-5045c8ed9afd4920b43f310298c0fcfc
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822414B2

Reaction notes

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