Sulfuric Acid → (S)-3-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile

To a solution of (S)-N-((S)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-2-hydroxy-2-phenylacetamide (2.5 g, 8.14 mmol), prepared as described in Example 1E, in EtOH (25 mL) was added 15% aqueous sulfuric acid (25 mL). The resulting mixture was refluxed overnight, then cooled to RT. After removal of most of the EtOH, the mixture was diluted with water (200 mL), extracted with CH2Cl2 (3×50 mL). The aqueous layer was basified with 4N NaOH to pH=10, then extracted with CH2Cl2 (3×50 mL). The combined organics were washed with saturated aqueous NaCl dried (Na2SO4) and concentrated. The residue was crystallized from EtOAc/hexanes to afford the title compound (1.026 g, 73% yield). LC/MS (method A): retention time=0.95 min, (M+H)+=174.

1. temperatureThe resulting mixture was refluxed overnight
2. customAfter removal of most of the EtOH
3. additionthe mixture was diluted with water (200 mL)
4. extractionextracted with CH2Cl2 (3×50 mL)
5. extractionextracted with CH2Cl2 (3×50 mL)
6. washThe combined organics were washed with saturated aqueous NaCl
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customThe residue was crystallized from EtOAc/hexanes

ORD record

ord-4a557fba27ed41cdb6671bfe784ef7b5

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709647B2