Ammonium Hydroxide → HCID 118498652, compound

HRID 1486937Notes

Reaction equation

HRID 1486937 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][CH:7]=[C:6]([C:13](O)=O)[C:5]2=O.S(Cl)([Cl:19])=O.[OH-:21].[NH4+:22]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:22]=[CH:13][C:6]([C:7]([NH2:8])=[O:21])=[C:5]2[Cl:19]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 103996599HCID 103996599, compound

Product 1

HCID 118498652HCID 118498652, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF (0.5 mL) was added to a stirred suspension of 6-bromo-7-fluoro-4-oxo-1H-quinoline-3-carboxylic acid (22.5 g, 78.66 mmol) in thionyl chloride (140 g, 1179.85 mmol) and the mixture heated to reflux for 2 h. The reaction was allowed to cool concentrated in vacuo and the residue azeotroped twice with toluene to afford a yellow solid. This solid was added portion wise to a solution of ammonium hydroxide (147 mL, 1179.85 mmol) at 0° C. The white suspension was stirred for 15 minutes then the solid filtered, washed with water and dried under vacuum to afford the desired material (23.80 g, 100%) as a white powder. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 8.92 (1H, s), 8.59 (1H, d), 8.21 (1H, s), 8.09 (1H, d), 7.98 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=304.8.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. customthe residue azeotroped twice with toluene
  6. customto afford a yellow solid
  7. filtrationthe solid filtered
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-0458e5ee27724c9b82a28f3e93f8eb41
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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