Sodium Hydroxide → HCID 178418887, compound

HRID 9480Notes

Reaction equation

HRID 9480 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[CH2:10][C:11]([OH:13])=O.[OH-].[Na+]>Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:8]=[C:9]([OH:14])[CH:10]=[C:11]2[OH:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21984308Propanoic acid, 3-[(2-bromophenyl)amino]-3-oxo-

Product 1

HCID 178418887HCID 178418887, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
140 °C

Procedure

N-(2-Bromophenyl)malonamic acid (43 g, 170 mmol), polyphosphoric acid (334 mL of 0.5 M), and hydrochloric acid (444 mL of 1 N) were combined and heated at 140° C. for three hours. The solution was allowed to cool to ambient temperature, and additional hydrochloric acid (603 mL of 1 N) was added. The reaction was stirred for four hours and then adjusted to pH 4 with the addition of 20% aqueous sodium hydroxide. A precipitate formed and was isolated by filtration, washed with water, and dried to provide 37.4 g of 8-bromoquinoline-2,4-diol as a solid.

Workup

  1. temperatureto cool to ambient temperature
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-69f9ed9971d84108bc0b47b3fce1fc7f
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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