Ammonium Hydroxide → HCID 68579214, compound

HRID 643297Notes

Reaction equation

HRID 643297 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:7]2O.P(Br)(Br)([Br:21])=O.[OH-].[NH4+]>CN(C=O)C>[Br:21][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[N:9][C:8]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24613Phosphorus oxybromideHCID 178515335HCID 178515335, compound

Product 1

HCID 68579214HCID 68579214, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-chloro-3-phenylcinnolin-4-ol (2.40 g, 9.3 mol) and POBr3 (10.0 g, 35 mmol) in DMF (100 mL) was heated to 50° C. for 2 hours. The reaction was poured into ice-water, adjusted to pH to ˜10 by diluted ammonium hydroxide and extracted with ethyl acetate. The combined organics were concentrated to yield 4-bromo-8-chloro-3-phenyl-cinnoline (1.40 g) as a pale yellow solid. MS m/z 321, 323 [M+H]+;

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-489badaadab34c76a70b686b8ae379fc
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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