Ammonium Acetate → 4-Chloro-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

HRID 970536Notes

Reaction equation

HRID 970536 reaction equation
C([O-])(=[O:3])C.[NH4+].Cl[C:7]1[C:16]([C:17]#[N:18])=[C:15]([Cl:19])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:20])[CH:13]=2)[N:8]=1>C(O)(=O)C>[Cl:19][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:20])[CH:13]=2)[NH:8][C:7](=[O:3])[C:16]=1[C:17]#[N:18]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 210819292,4-Dichloro-6-methylquinoline-3-carbonitrile

Product 1

HCID 210819634-Chloro-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

Ammonium acetate was added to a suspension of Compound 105 (7.1 g, 29.95 mmol) in glacial acetic acid and heated at 140° C. for 4 h. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried under vacuum to yield 4.5 g (69%) of white solids. M.P. 264° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 7.34 (d, J=8.4 Hz, 1H), 7.63 (dd, J=1.5, 8.4 Hz, 1H), 7.75 (s, 1H). EIMS m/z 219 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-244910db77d7466e9a6445bf2b501cd8
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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