Carbon Dioxide → 8-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

HRID 971490Notes

Reaction equation

HRID 971490 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[C:12]1([Li])C=CC=CC=1.[C:19](=[O:21])=[O:20]>CCOCC>[CH3:12][O:20][C:19]([CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:21]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineHCID 178506676HCID 178506676, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 3-necked flask is charged with 3-methyl-5,6,7,8-tetrahydroquinoline (45 g. 0.29 moles) and ether (400 ml). Phenyl lithium solution (330 ml. of a 1 molar solution 0.3 moles in ether is added to the stirred solution at a rate to give gentle reflux. Reflux is maintained for 2 hours. After cooling in an ice-bath CO2 is bubbled through the resulting red solution of 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline till no further colour change. The mixture is further treated with methanolic HCl as described in Example 24 of copending U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Workup

  1. customto give gentle reflux
  2. temperatureReflux
  3. temperatureis maintained for 2 hours
  4. customis bubbled through the resulting red solution of 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline till no further colour change
  5. additionThe mixture is further treated with methanolic HCl

Sources & evidence

ORD record
ord-8ab8818c43d54e258e19c9d2a23f4b68
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

Loading…