4-Methylmorpholine → Methyl 2-amino-4-(hydroxymethyl)benzoate

Temperatur

-15 °C

To a solution of 1-methyl 2-aminoterephthalate (10.0 g, 51.2 mmol) and NMM (5.75 mL, 1 equiv) in DME (90 mL) at −15° C. was added dropwise IBCl (6.7 mL, 1 equiv). The mixture was stirred at this temperature for 15 min. The salt was removed by filtration and the solution was cooled down to −15° C. A solution of NaBH4 (3.06 g, 1.5 equiv) in water (30 mL) was added carefully dropwise. At the end of the addition, water (100 mL) was added and the mixture was stirred at r.t. for 15 min. Aq NaOH (2N, 50 mL) was added and the aqueous phase was extracted twice with AcOEt. The organic phase were combined and dried (Na2SO4). The solution was concentrated in vacuo to afford a white solid (8.0 g, 86%) (ES-MS: m/z 182.1 [M+H]+, rt 3.50 min).

1. customThe salt was removed by filtration
2. additionwas added
3. stirringthe mixture was stirred at r.t. for 15 min
4. extractionthe aqueous phase was extracted twice with AcOEt
5. dry with materialdried (Na2SO4)
6. concentrationThe solution was concentrated in vacuo

ORD-Eintrag

ord-cb56a9e4621b4309afd2448643e00c06

Quelldatensatz

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07655666B2