Hydrochloric Acid → HCID 67289758, compound

HRID 1036962Notes

Reaction equation

HRID 1036962 reaction equation
Cl.[CH3:2][C:3]1([CH3:24])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[CH2:4]1>C(O)C.O.[Fe]>[NH2:21][C:17]1[CH:16]=[C:15]([CH:5]2[CH2:4][C:3]([CH3:2])([CH3:24])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=3)[NH:6]2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67290202HCID 67290202, compound

Product 1

HCID 67289758HCID 67289758, compoundYield 92.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a round bottom flask, iron powder (9.13 g, 162.7 mmol) and concentrated hydrochloric acid (0.16 mL) were added to a mixture of 4,4-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (5 g, 16.3 mmol) in ethanol (50 mL) and water (12 mL). The resultant mixture was allowed to stir at reflux for 1.5 h. The mixture was filtrated and the filtered cake was washed by ethanol several times. The ethanol was removed under vacuum. The residue was dissolved in ethyl acetate (100 mL) and water (50 mL), separated the organic layer. The organic layer was washed by brine twice and dried over anhydrous sodium sulfate. Filtered and concentrated to provide 2-(3-amino-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile as yellow solid (4.2 g, yield: 85%). MS (ESI+APCI) 278.2.

Workup

  1. temperatureat reflux for 1.5 h
  2. filtrationThe mixture was filtrated
  3. washthe filtered cake was washed by ethanol several times
  4. customThe ethanol was removed under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  6. customwater (50 mL), separated the organic layer
  7. washThe organic layer was washed by brine twice
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationFiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f8e5a9aea2fe4e6d96bf166c355c4260
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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