Triethylamine → HCID 178507923, compound

HRID 1295451Notes

Reaction equation

HRID 1295451 reaction equation
[Br:1][C:2]1[CH:13]=C[C:5]2NC(=O)OC(=O)[C:4]=2[CH:3]=1.[C:14](#N)[CH:15]([CH2:17][C:18]#[N:19])[OH:16].C([N:23](CC)CC)C>CN(C=O)C>[NH2:23][C:18]1[CH:17]=[C:15]([OH:16])[C:14]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:13]=2)[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2885615-Bromoisatoic AnhydrideHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 178507923HCID 178507923, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 6-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (90 g, 0.373 mol) in (N,N-dimethylformamide) (DMF) (400 ml) was added to a solution of malonitrile (37 g, 0.41 mol) and triethylamine (41.4 g, 0.41 mol) in DMF (150 ml) at 50–60° C. The reaction mixture was maintained at 50–60° C. for 30 min. A reverse quench into ice-cold 0.2N HCl (400 ml) produced a precipitate. This material was isolated by filtration and vacuum dried. It was then dissolved in 8 N KOH (2 l) and the solution was refluxed for 40 h. After cooling to rt, the mixture was neutralized with HCl, and the resulting precipitate was filtered and air dried to afford 2-amino-6-bromo-quinolin-4-ol as a pale yellow solid (95 g, 97%). This material was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was maintained at 50–60° C. for 30 min
  2. customA reverse quench into ice-cold 0.2N HCl (400 ml)
  3. customproduced a precipitate
  4. customThis material was isolated by filtration and vacuum
  5. customdried
  6. dissolutionIt was then dissolved in 8 N KOH (2 l)
  7. temperaturethe solution was refluxed for 40 h
  8. filtrationthe resulting precipitate was filtered
  9. customair dried

Sources & evidence

ORD record
ord-66325c64aee74445acb7bbb4da6e97d1
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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