Sodium Hydroxide → 6-Bromo-4-chlorocinnoline

HRID 2307778

Reaction equation

HRID 2307778 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6][C:5]2=O.[OH-].[Na+].O=P(Cl)(Cl)[Cl:17]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[C:5]2[Cl:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2709026-Bromo-4-cinnolinol

Product 1

HCID 124480786-Bromo-4-chlorocinnolineYield 43%

Conditions

Temperature
0 °C

Procedure

A solution of Example 34C (0.4 g, 1.8 mmol) in POCl3 (2.5 mL) was heated to 100° C. for 2 hours, and poured slowly onto ice. The aqueous layer was cooled to 0° C. and adjusted to pH 5-7 with 50% NaOH. The aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined organic layers were concentrated. The residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide the desired product (0.190 g, 43%).

Workup

  1. additionpoured slowly onto ice
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. concentrationthe combined organic layers were concentrated
  4. customThe residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-8e45b3c3aee24d2191646d7def1850e8
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Linked notes

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