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

HRID 44403Notes

Reaction equation

HRID 44403 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])(=[O:17])C.[NH4+]>C(O)(=O)C>[Cl:14][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:17])[C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

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

Product 1

HCID 27775104-Chloro-1,2-dihydro-2-oxoquinoline-3-carbonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,4-dichloroquinoline-3-carbonitrile (Example 72a) (0.95 g, 4.26 mmol) and ammonium acetate (0.36 g, 4.67 mmol) were heated in acetic acid (20 mL) at 140° C. for 4 hours, then cooled to room temperature. The reaction was poured into ice water (400 mL), and the resultant precipitate was collected by filtration to give 4-chloro-2-oxo-1,2-dihydroquinoline-3-carbonitrile (0.668 g, 77%) as a light yellow solid. M.p.: >250° C. 1H NMR (400 MHz, DMSO-d6) δ7.42 (m, 2H), 7.79 (m, 1H), 7.96 (d, J=8.4 Hz, 1H), 12.72 (s, 1H). MS 205 (MH+)

Workup

  1. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-472c88d0b3554ec1b5f09e0349b829cd
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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