Sodium Hydroxide → 6-Carboxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

HRID 2074009Notes

Reaction equation

HRID 2074009 reaction equation
[C:1]([C:5]1[C:6]([O:16][CH3:17])=[C:7]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][CH2:10][CH2:9][CH2:8]2)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([C:5]1[C:6]([O:16][CH3:17])=[C:7]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][CH2:10][CH2:9][CH2:8]2)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 148832316-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

Product 1

HCID 148832326-Carboxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the compound of step 5 above (1.1 g), 10% aqueous NaOH (20 ml) and MeOH (40 ml) is stirred under reflux for 30 minutes. The MeOH is evaporated and the aqueous residue partitioned with CHCl3. The mixture is stirred vigorously, cooled to 0° C. and treated with 10% HCl (28 mls). The aqueous layer is separated and the organic layer is dried and evaporated. The residue is crystallized from ether affording the desired product, M.P. 129°-132° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe MeOH is evaporated
  3. customthe aqueous residue partitioned with CHCl3
  4. stirringThe mixture is stirred vigorously
  5. additiontreated with 10% HCl (28 mls)
  6. customThe aqueous layer is separated
  7. customthe organic layer is dried
  8. customevaporated
  9. customThe residue is crystallized from ether affording the desired product, M.P. 129°-132° C.

Sources & evidence

ORD record
ord-3c2d61108b674c17b1bac65668b3200a
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

Loading…