Water → HCID 59170067, compound

Temperature

60 °C

Methyl 3-oxoheptanoate (0.16 g, 1 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.12 g, 1 mmol) was mixed and heated for 1 h at 60° C. The bright yellow oil was dissolved in methanol (2 mL) and water (1 mL) whereby and hydroxylamine hydrochloride (0.07 g, 1 mmol) was added, resulting in a pH of ca 5. The reaction was heated at 60° C. for 3 days. The solvents were evaporated and the residue refluxed in acetic acid: conc. HCL (1+1 mL) for 4 h. The solvents were evaporated to dryness and the residue dissolved in water at ca pH 10, filtered and acidified with HCl and extracted to DCM, dried (Na2SO4) and evaporated to yield the title compound as a light brown solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.93 (t, J=7.32 Hz, 3 H) 1.33-1.45 (m, 2 H) 1.69-1.78 (m, 2 H) 3.12 (t, J=7.57 Hz, 2 H) 8.50 (s, 1H)

1. customresulting in a pH of ca 5
2. temperatureThe reaction was heated at 60° C. for 3 days
3. customThe solvents were evaporated
4. temperaturethe residue refluxed in acetic acid
5. customThe solvents were evaporated to dryness
6. dissolutionthe residue dissolved in water at ca pH 10
7. filtrationfiltered
8. extractionextracted to DCM
9. dry with materialdried (Na2SO4)
10. customevaporated

ORD record

ord-4dcefb9141054ac8ba9004425e6b8a1f

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07666888B2