Acetic Acid → HCID 9942957, compound

HRID 2213786Notes

Reaction equation

HRID 2213786 reaction equation
C([Li])CCC.[C:6](#[N:8])[CH3:7].CN(/[CH:12]=[N:13]/[C:14]1[C:15]([C:26]([O:28]C)=O)=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([O:24][CH3:25])=[CH:19][CH:18]=2)C.C(O)(=O)C>O1CCCC1>[CH3:25][O:24][C:20]1[CH:19]=[CH:18][C:17]2[CH:16]=[C:15]3[C:14](=[CH:23][C:22]=2[CH:21]=1)[NH:13][CH:12]=[C:7]([C:6]#[N:8])[C:26]3=[O:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 178418339ButyllithiumHCID 178496935HCID 178496935, compound

Product 1

HCID 9942957HCID 9942957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2.81 mL (7.03 mmol) of n-butyllithium (2.5M in hexane) in 2.0 mL of tetrahydrofuran at −78° C. is added dropwise a solution of 0.448 mL (8.44 mmol) of acetonitrile in 4.4 mL of tetrahydrofuran. After completion of addition, the suspension is stirred for 10 minutes. To this is added 804.5 mg (2.81 mmol) of methyl 3-{[(E)-(dimethylamino)methylidene]amino}-6-methoxy-2-naphthoate in 18 mL of tetrahydrofuran dropwise. The resulting reaction mixture is stirred at −78° C. for 1 hour and at −5° C. for 1 hour. The reaction mixture is again cooled to −78° C. and 4.0 mL (69.9 mmol) of acetic acid is added dropwise. The reaction mixture is warmed up to room temperature and stirred overnight. The precipitate is collected by filtration and washed sequentially with water, acetonitrile and methanol. After drying in vacuo, this yields 468.6 mg (67%) of 8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile as a yellow solid, mp>265° C.

Workup

  1. additionAfter completion of addition
  2. customThe resulting reaction mixture
  3. stirringis stirred at −78° C. for 1 hour and at −5° C. for 1 hour
  4. temperatureThe reaction mixture is warmed up to room temperature
  5. stirringstirred overnight
  6. filtrationThe precipitate is collected by filtration
  7. washwashed sequentially with water, acetonitrile and methanol
  8. customAfter drying in vacuo

Sources & evidence

ORD record
ord-8a45aab37a0648a2bd3f68b191818d8c
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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