Pyridine → Butyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

HRID 597196Notes

Reaction equation

HRID 597196 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]([CH3:15])[CH2:7][C:6]2=[O:16].N1C=CC=CC=1.Cl[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH:8]([CH3:15])[CH2:7][C:6]2=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61140Butyl chloroformateHCID 214397206,7-Dimethoxy-2-methyl-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 21439716Butyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled mixture of 1.15 g. (5.17 mmol) of the quinoline product of Example 4, 751 mg. (10.15 mmol) of dry pyridine and 5.5 ml. of methylene chloride stirred under a nitrogen atmosphere was added dropwise 1.03 g. (7.60 mmol) of butyl chloroformate in 1 ml. methylene chloride over 10 min. at a rate to maintain a 10°-15° temperature. After the addition was complete the bath was removed, the reaction stirred at room temperature for 45 min., and poured onto 25 ml. saturated sodium bicarbonate solution. The organic phase was collected and washed with 25 ml. of saturated sodium bicarbonate solution, 50 ml. saturated sodium chloride solution, dried over magnesium sulfate, then gravity filtered and evaporated to a viscous amber oil. Evaporative distillation at 110° C (0.05 mm) gave 1.4 g. of a very viscous amber oil.

Workup

  1. additionTo a cooled mixture of 1.15 g
  2. additionwas added dropwise 1.03 g
  3. additionAfter the addition
  4. customwas removed
  5. additionpoured onto 25 ml
  6. customThe organic phase was collected
  7. washwashed with 25 ml
  8. dry with materialsaturated sodium chloride solution, dried over magnesium sulfate
  9. filtrationgravity filtered
  10. customevaporated to a viscous amber oil
  11. distillationEvaporative distillation at 110° C (0.05 mm)
  12. customgave 1.4 g

Sources & evidence

ORD record
ord-eb2f65428b984a76bcaa1cf28e0417dc
Source dataset
uspto-grants-1977_03
Patent number
US04013662

Reaction notes

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