Ethyl cyanoacetate → HCID 67285814, compound

HRID 1618571Notes

Reaction equation

HRID 1618571 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])O[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.[C:14]([CH2:16]C(OCC)=O)#[N:15].C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:13]=[C:6]2[C:5]([C:10]([OH:11])=[C:16]([C:14]#[N:15])[C:8](=[O:12])[NH:7]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 67285814HCID 67285814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (515 mg, 2.8 mmol) (commercially available through AstaTech™, Inc.), ethyl 2-cyanoacetate (303 μL, 2.8 mmol), and triethylamine (793 μL, 5.7 mmol) in DMF (1.4 mL) was stirred at 120° C. for 6 h. The reaction mixture was then concentrated. Upon addition of 1M HCl a precipitate formed, which was isolated by filtration and dried under vacuum, affording 7-fluoro-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile. Mass Spectrum (ESI) m/e=205 (M+1).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionUpon addition of 1M HCl a precipitate
  3. customformed
  4. customwhich was isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d79ba0cee80b4f8baf70074d87535bdf
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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