Acetic Acid → 4-Oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 2213714Notes

Reaction equation

HRID 2213714 reaction equation
C([Li])CCC.[C:6](#[N:8])[CH3:7].CN([CH:12]=[N:13][C:14]1[C:15]([C:24]([O-:26])=O)=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)C.C(O)(=O)C>O1CCCC1.O>[O:26]=[C:24]1[C:15]2[C:14](=[CH:23][C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:16]=2)[NH:13][CH:12]=[C:7]1[C:6]#[N:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 219564743-{[(Dimethylamino)methylidene]amino}-2-naphthoateHCID 178418339Butyllithium

Product 1

HCID 98344134-Oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of 5.6 g (30 mmol) of 3-amino-2-napthoic acid in 30 mL of N,N-dimethylformamide dimethyl acetal is refluxed for 6 hours. Removal of the solvent yields 7.06 g (86.4%) of methyl 3-{[(dimethylamino)methylidene]amino}-2-naphthoate as a dark oil residue. To a solution of 20.8 mL (52 mmol) of n-butyllithium (2.5M in hexane) in 18 mL of tetrahydrofuran (THF) is added dropwise a solution of 5.97 mL (114 mmol) of acetonitrile in 100 mL of THF at −78° C. After completion of addition, the suspension is stirred for 15 minutes. To this is added 7.02 g (26 mmol) of 3-{[(dimethylamino)methylidene]amino}-2-naphthoate in 50 mL of THF dropwise. The resulting reaction mixture is stirred at −78° C. for 1 hour. Then 7.8 g (130 mmol) of acetic acid is added dropwise. The reaction mixture is warmed up to room temperature and diluted with water. The precipitate is collected by filtration and washed with water and ethyl acetate. After drying in vacuo, this yields 3.80 g (67%) of the product as a yellow solid, mp>260° C.

Workup

  1. additionAfter completion of addition
  2. customThe resulting reaction mixture
  3. stirringis stirred at −78° C. for 1 hour
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water and ethyl acetate
  6. customAfter drying in vacuo

Sources & evidence

ORD record
ord-bfc0d4cfc2f540998db7d2cbf893ddfe
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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