Methyl chloroformate → 8-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

HRID 482979Notes

Reaction equation

HRID 482979 reaction equation
[Li][C:2]1([Si](C)(C)C)[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.Cl[C:18]([O:20][CH3:21])=[O:19]>C1COCC1>[CH3:21][O:20][C:18]([CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)=[O:19]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 178506786HCID 178506786, compound

Product 1

HCID 122789608-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Lithio-5,6,7,8-tetrahydro-3-methyl-8-trimethylsilylquinoline, prepared as in Example 3, is treated with 1 equivalent of methyl chloroformate in THF at -20° C. under nitrogen. After the addition the mixture is allowed to warm to ambient temperature and the solvent removed by evaporation. The residue is dissolved in 2NHCl and washed with ether basified with Na2CO3 and extracted with chloroform. The extracts are dried and evaporated. Distillation of the residue gives the title compound as a pale yellow oil bp 120°/0.25 mm.

Workup

  1. additionAfter the addition the mixture
  2. customthe solvent removed by evaporation
  3. dissolutionThe residue is dissolved in 2NHCl and
  4. washwashed with ether
  5. extractionextracted with chloroform
  6. customThe extracts are dried
  7. customevaporated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-c6f3ec75ea354bae81334f56ac1b2248
Source dataset
uspto-grants-1986_03
Patent number
US04577022

Reaction notes

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