Acetic Acid → HCID 178492555, compound

HRID 1935067Notes

Reaction equation

HRID 1935067 reaction equation
C([Li])CCC.[C:6](#[N:8])[CH3:7].CO[C:11](=[O:27])[C:12]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([O:20][CH3:21])[C:13]=1[N:22]=[CH:23]N(C)C.C(O)(=O)C>O1CCCC1.O>[OH:27][C:11]1[C:12]2[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[N:22]=[CH:23][C:7]=1[C:6]#[N:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 543703152-(Dimethylamino-methyleneamino)-3,6-dimethoxy-benzoic acid methylesterHCID 178418339Butyllithium

Product 1

HCID 178492555HCID 178492555, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To 12.5 ml of tetrahydrofuran at −78° C. was added 8.8 ml of 2.5M n-butyllithium in hexanes. Then 1.18 ml of acetonitrile in 25 ml of tetrahydrofuran was added dropwise. The mixture was stirred at −78° C. for 15 minutes. Then a solution of 2-(dimethylamino-methyleneamino)-3,6-dimethoxy-benzoic acid methylester in 62 ml of tetrahydrofuran was added dropwise. The mixture was stirred at −78° C. for 10 minutes, then warmed to room temperature in 15 minutes. Acetic acid (3 ml) was added, followed by 200 ml of water. The product was collected, washed with water, and dried to give 1.57 g of 4-hydroxy-5,8-dimethoxy-quinoline-3-carbonitrile as a solid, mp 300-305° C.; mass spectrum (EI, m/e): M 230.0685.

Workup

  1. stirringThe mixture was stirred at −78° C. for 10 minutes
  2. temperaturewarmed to room temperature in 15 minutes
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6308599ab8e54a67bc720f5ba5a4f032
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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