Hydrochloric Acid → 4-Chloroquinolin-6-amine

HRID 408651Notes

Reaction equation

HRID 408651 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12]C(=O)C)[CH:10]=2)[N:5]=[C:4](C)[CH:3]=1.[ClH:17]>CO>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[Cl:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178474057HCID 178474057, compound

Product 1

HCID 687284244-Chloroquinolin-6-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(4-Hydroxy-2-methylquinolin-6-yl)acetamide (0.05 g; see step (i) above), methanol (2 mL) and 5 N hydrochloric acid (6 mL) was refluxed for 90 minutes. The reaction mixture was evaporated and the residue dissolved in ethyl acetate and sodium carbonate solution. The organic phase was washed with water, dried (Na2SO4), filtered and concentrated to give the sub-title compound as a pale yellow solid.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-97ecbca0bc5e4d15a2208d4749715aff
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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