P-Anisidine → HCID 55034743, compound

The compound was prepared according to literature procedure. To a solution of cyclopropane-1,1-dicarboxylic acid (390.0 mg, 3.0 mmol) in dry THF (20 mL) in ice bath was added triethylamine (TEA; 0.40 mL, 3.1 mL) dropwise. The solution was stirred for 15 min and SOCl2 (0.20 mL, 2.9 mmol) was added to it. After 15 min reaction at such temperature, a solution of p-anisidine (387.0 mg, 3.1 mmol) in THF (5 mL) was added slowly. Reaction mixture was allowed to warm to rt and stirred for additional 18 h. After that, reaction mixture was diluted by EA; unconsumed diacid was quenched by 10% NaOH (0.5 mL). Crude product was extracted by EA and washed by water and brine. Organic portions were concentrated in vacuo. Solid precipitated by addition of n-heptane was collected by filter. Prolonged drying in vacuo gave the title compound. YD: 82%; mp 133-136° C. 1H-NMR (400 MHz, DMSO-d6) δ: 1.40 (s, 4H, 2×CH2), 3.71 (s, 3H, OCH3), 6.85 (d, J=8.8 Hz, 2H, ArH), 7.49 (d, J=8.8 Hz, 2H, ArH), 10.42 (s, 1H, NH). Anal. (C13H13NO4.0.5; H2O) C, H, N. MS (ESI) 233.8 (M−H)−.

1. customThe compound was prepared
2. customAfter 15 min reaction at such temperature
3. customReaction mixture
4. stirringstirred for additional 18 h
5. customAfter that, reaction mixture
6. customunconsumed diacid was quenched by 10% NaOH (0.5 mL)
7. extractionCrude product was extracted by EA
8. washwashed by water and brine
9. concentrationOrganic portions were concentrated in vacuo
10. customSolid precipitated by addition of n-heptane
11. customwas collected
12. filtrationby filter
13. customProlonged drying in vacuo

ORD record

ord-3f6c04e86e5f4163b014913730b37344

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946282B2