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

HRID 1363082Notes

Reaction equation

HRID 1363082 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-b7e2848c3292452b94c34eeed4b56f0b
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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