Methyl cyanoacetate → 5-Fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

HRID 1848633Notes

Reaction equation

HRID 1848633 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[C:11]([CH2:13][C:14](OC)=[O:15])#[N:12].C[O-].[Na+]>CO>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]2[C:3]=1[CH:4]=[C:13]([C:11]#[N:12])[C:14](=[O:15])[NH:1]2

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 10942334Sodium MethoxideHCID 217194752-Amino-6-fluorobenzaldehyde

Product 1

HCID 686018505-Fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrileYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of MeOH (60 mL) containing 2-amino-6-fluoro-benzaldehyde (1.19 g, 8.6 mmol) and methyl cyanoacetate (0.91 mL, 10.3 mmol) was added sodium methoxide (2.93 mL, 12.8 mmol, 25% in MeOH). The mixture was stirred at rt for 16 hrs. The resulting yellow precipitates were filtered, washed with MeOH and then stirred in 1N HCl (75 mL) for 2 hrs at rt. The solid was filtered, washed with water and dried in vacuo to yield 5-fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrile (1.2 g) as a white solid. MS [M+H]+: 189.1; tR=2.00 min. (method 1)

Workup

  1. customThe resulting yellow precipitates
  2. filtrationwere filtered
  3. washwashed with MeOH
  4. stirringstirred in 1N HCl (75 mL) for 2 hrs at rt
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e88d2bcd045d4a978bd984e23051ea62
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

Loading…