Ammonium Acetate → 4-Chloro-1,2-dihydro-2-oxoquinoline-3-carbonitrile

HRID 970544Notes

Reaction equation

HRID 970544 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]=[CH:12][CH:13]=2)[N:8]=1>C(O)(=O)C>[Cl:19][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:3])[C:16]=1[C:17]#[N:18]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 27851312,4-Dichloroquinoline-3-carbonitrile

Product 1

HCID 27775104-Chloro-1,2-dihydro-2-oxoquinoline-3-carbonitrileYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

Ammonium acetate (2.1 g, 27 mmol) was added to a suspension of Compound 114 (6.0 g, 27 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 5.2 g (94%) of white solids. M.P. 302° C. 1H NMR (DMSO-d6): δ 1H-NMR (DMSO-d6): 7.4 (m, 2H), 7.79 (t, J=7.6 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H); EIMS: 205 (M+H).

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-52ec49a2b9084969b2d84290faacd304
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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