Ammonia → HCID 58085692, compound

HRID 1907255Notes

Reaction equation

HRID 1907255 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH3:13])[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2O.P(Cl)(Cl)([Cl:22])=O.N>>[Cl:22][C:5]1[C:4]2[C:9](=[CH:10][C:11]([F:12])=[C:2]([F:1])[CH:3]=2)[N:8]=[C:7]([CH3:13])[C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178469185HCID 178469185, compound

Product 1

HCID 58085692HCID 58085692, compound

Procedure

A suspension of 4-hydroxy quinoline 60 was refluxed with phosphorus oxychloride for 30 minutes. To the cooled reaction mixture was added aqueous ammonia and the product was obtained by extracting with methylene chloride, dried over sodium sulfate and concentrated in vacuo. 1H NMR (CDCl3) δ (ppm): 1.44 (3H, t, J=7.14 Hz), 2.70 (3H, s), 4.50 (2H, q, J=7.14 Hz), 7.62 (1H, t, J=7.69 Hz), 7.78 (1H, dd, J=10.71, 7.69 Hz), 7.95 (2H, d, J=10.72, 8.24 Hz). m/z 286.7 (MH+).

Workup

  1. customTo the cooled reaction mixture
  2. customthe product was obtained
  3. extractionby extracting with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f973f282fa03430294b75e63d12edbcb
Source dataset
uspto-grants-2013_12
Patent number
US08598159B2

Reaction notes

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