P-Anisidine → HCID 86134692, compound

Temperature

60 °C

Ethyl 2-bromoacetate (146 mL, 1.3 mol) was added dropwise to a stirred solution of 4-methoxyaniline (3) (75 g, 0.61 mol) and DIPEA (265 mL, 1.5 mol) in MeCN (300 mL). The reaction mixture was stirred at 60° C. for 16 h and then partitioned between 2 M HCl (aq.) (500 mL), and EtOAc (300 mL), the aqueous phase was extracted with EtOAc (300 mL) and the combined organics were washed succesively with 2 M HCl (aq.) (2×300 mL), water (500 mL), and brine (500 mL), dried (MgSO4), filtered and solvents removed in vacuo to give diethyl 2,2′-((4-methoxyphenyl)azanediyl)diacetate (4) (180 g, 100%) as a purple oil: m/z 296 (M+H)+ (ES+). 1H NMR (400 MHz, CDCl3) δ 6.82-6.78 (m, 2H), 6.64-6.59 (m, 2H), 4.19 (q, J=7.1 Hz, 4H), 4.10 (s, 4H), 3.74 (s, 3H), 1.27 (t, J=7.1 Hz, 6H).

1. custompartitioned between 2 M HCl (aq.) (500 mL), and EtOAc (300 mL)
2. extractionthe aqueous phase was extracted with EtOAc (300 mL)
3. washthe combined organics were washed succesively with 2 M HCl (aq.) (2×300 mL), water (500 mL), and brine (500 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customsolvents removed in vacuo

ORD record

ord-c668d14c98ee4827ac19b998255876a5

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221756B2