Ammonium Acetate → HCID 59699556, compound

HRID 901242Notes

Reaction equation

HRID 901242 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](=[N: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](=[N: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 59699635HCID 59699635, compound

Product 1

HCID 59699556HCID 59699556, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

Ammonium acetate (6.81 g, 88.37 mmol) was added to a suspension of 2,4-Dichloro-[1,8]-naphthyridine-3-carbonitrile (30) in acetic acid at room temperature and heated at 140° C. for 45 min. The solution was cooled and poured into ice water. The solids formed were filtered, washed with cold water and suspended in saturated sodium bicarbonate solution. After stirring overnight at room temperature, the solids were filtered, washed by cold water, and dried at room temperature under vacuum to yield 8.0 g (48%) of 4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (31) as white solids. MP: 310° C.; 1H-NMR (DMSO-d6): δ 7.58 (dd, J=4.4, 8.0 Hz, 1H), 8.50 (d, J=2.0, 8.0 Hz, 1H), 8.83 (dd, J=4.4, 1.6 Hz, 1H), 13.03 (S, 1H); EIMS: 206 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed with cold water
  5. filtrationthe solids were filtered
  6. washwashed by cold water
  7. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-d8bd9ea4e24b41c69a08579367244d5c
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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