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

HRID 1643862Notes

Reaction equation

HRID 1643862 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][C@@H:7]([NH:13]C(=O)[C@@H](O)C1C=CC=CC=1)[CH2:6]2)#[N:2].S(=O)(=O)(O)O>CCO>[NH2:13][C@H:7]1[CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:9][CH2:8]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66757271(S)-N-((S)-6-Cyano-1,2,3,4-tetrahydroquinolin-3-yl)-2-hydroxy-2-phenylacetamide

Product 1

HCID 66757521(S)-3-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1E (2.5 g, 8.14 mmol) 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 brine, dried (Na2SO4) and concentrated. The residue was crystallized from EtOAc/hexane to afford the title compound (1.026 g, 73% yield).

Workup

  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 brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-dfe5bb16074649df984fca84fc45d18c
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

Loading…